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Entourage Mac for Exchange Servers
Tips and Reports

Last updated February 21, 2011

On this Page:

Related Links at MacWindows

Cross-platform Entourage info at other sites

In a TechXworld article called Supporting Macs on Exchange Server, John Rizzo describes the various options for using the Mac as a client to Exchange Server. The story describes the different approaches for Intel and PowerPC Macs and the pros and cons of each.

A reader posting at the O'Reilly web site describes how to move Outlook for Windows email messages to Entourage.

A web site called the Entourage Help Page has directions on questions that readers frequently ask us. One page describes how to copy messages or contacts from Entourage to Outlook for Windows.

Another page at this site describes several methods of moving mail from Outlook for Windows to Entourage.

Going from Mac to PC, a page describing moving Entourage email to Outlook for Windows.

A third page on cross-platform Entourage issues describes these tasks:

  • Import a windows based *.pst file
  • Import .eml file
  • Import holidays from Outlook on a PC into Entourage
  • Export Entourage Contact List and import it into Outlook for Windows XP
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Microsoft Outlook has traditionally been the Windows client for Microsoft's Exchange Server for e-mail and calendar functions. Microsoft never created a Mac OS X version of Outlook. The most recent version of Outlook for Mac, Outlook 2001, runs in Mac OS X's Classic mode. In 2001, Microsoft announced that it would transfer the responsibility for its Mac Exchange client from its Exchange group to the Macintosh Business Unit, the group that created Microsoft Office X. In February 2003, Microsoft announced that MBU decided to drop Outlook for Mac, and instead integrate functionality into the Entourage email/scheduling/contacts application.

For more info, see visit Microsoft's Entourage page.

Version History

MS security updates for Entourage 2008/WSE and Office 2004/2008. Wednesday, March 10, 2010 -- Yesterday, Microsoft released updates to all of its Office applications. The updates are Entourage 2008 Web Services Edition 13.0.4, Office 2008 for Mac 12.2.4, Microsoft's Office 2004 for Mac 11.5.8, and Open XML File Format Converter for Mac 1.1.4. The updates fix security holes to protect against malware.

The update for Office 2008 also includes some improvements for Excel 2008, including fixing issues that cause Excel to unexpectedly quit and to incorrect format imported text. It also improves performance of print drivers in Snow Leopard.

Open XML File Format Converter is a free utility that can convert newer Office formats (.docx, .xlsx, and .pptx) to the older formats (.doc, .xls, and .ppt).

Microsoft hints at time zone fix in new Entourage update. Wednesday, December 10, 2008 -- In updates to Office 2008 and 2004 this week, Microsoft alluded to an Entourage time zone fix that may (or may not) address reported problems involving time zones. There are two such issues: the "Casablanca" time zone problem with sync services, and the time zone problems with printing calendars. For Entourage, Microsoft simply said that the new version "provides updated time zone information." If you've had these problems, if these updates address them. Microsoft also said it fixed a Word bug that could cause a problem when moving a file to Windows.

Microsoft released Office 2008 for Mac 12.1.5 Update, Microsoft Office 2004 for Mac 11.5.3 Update, and Open XML File Format Converter for Mac 1.0.2, which converts the newer file formats (.docx, .xlsx, .pptx) to the older formats. The company said that all three updates improve stability, performance, and security, specifically "vulnerabilities that an attacker can use to overwrite the contents of your computer's memory with malicious code."

In Office 2004, the updates fix problems with Word and Excel unexpectedly quitting. Office 2008 has a bigger list of bug fixes, including an issue saving files in the older .doc format (Word 97-2004 format) that are moved to Windows. Microsoft said that "this update fixes an issue that causes some formatting issues when you save a Word document in the Word 97-2004 format and then reopen it in Word 2003 for Windows."

All three updates are available through the Office AutoUpdate feature or at the Microsoft Mactopia site.

Office Mac updates for stability and Entourage bugs; Open XML Converter also updated. Thursday, October 16, 2008 -- Microsoft has issued updates for Office, the Office 2008 for Mac 12.1.3 Update and the Office 2004 for Mac 11.5.2 Update. While the version for Office 2004 is mostly a security update, the Office 2008 update address reliability and stability and some Entourage/Exchange bugs, as well as security. All of the other Office apps were updated.

Office 2008 12.1.3 fixes a problem with Entourage and Exchange 2007 caused by the previous 12.1.2 update. When connecting to the server with a secure connection, an error message would appear saying that the "server name or IP address does not match the name or IP address on the server's certificate."

Several other Entourage bugs are fixed, including a problem with calendar events being duplicated in Outlook Web Access or in Microsoft Office Outlook 2007. Another issue involves the Entourage Account Setup Assistant, which has improved handling of SSL and Autodiscover of Public Folders.

In addition, Microsoft updated Open XML Converter to version 1.0.1. The Converter can translate Open XML files (.docx, .pptx, .xlsx) created in Office 2008 for Mac or Office 2007 for Windows. Open XML Converter converts the files to the older .doc, .ppt, and .xls formats. The update adds enhancements for stability, performance, and security, according to Microsoft.

If you've used these updates

Entourage 2008 adds kerberos and increased Exchange compatibility. Tuesday, January 15, 2008 -- Entourage 2008 can use kerberos to authenticate to Active Directory for single sign on and can authenticate to Exchange Server's global address list (GAL). Previous versions of Entourage could not be part of Active Directory single sign-ons. (The included Messenger for Mac 6.0, which is not new, also enables users to add contacts from the GAL to the Messenger contacts list.)

Entourage can take advantage of more of Exchange Server's features. Exchange 2007-compatible resource booking allows Entourage 2008 users to book rooms in a simple manner and without adding overhead to Entourage. A new Out of Office (OOF) Assistant enables users to set up their Exchange account to send a custom auto-reply message. Microsoft also said that calendar management actions such as Accept and Decline are more consistent with Outlook.

Click here for more on Entourage 2008.

Microsoft releases Office Mac 11.3.7 Update. August 21, 2007 -- Last week, Microsoft released Office 2004 for Mac 11.3.7 Update, which the company says fixes security and stability issues. Computerworld has a description of the security updates.

Office 11.3.6 Update fixes Entourage/Exchange folder bug. July 18, 2007 -- Microsoft has released Office 2004 11.3.6 Update aimed at Entourage and Excel. The update fixes an Entourage 2004 problem with Exchange Server. From the Readme file:

Microsoft exchange public folder data loss issue is fixed: This update fixes an issue that causes data loss when public folder users who have a permission level of "Editor" or greater use Entourage to empty the cache for all public folders on the server running Exchange Server.

The update also plugs a security hole that left Excel 2004 vulnerable to an attack that could overwrite the Mac memory with malicious code.

Microsoft said that the previous update, 11.3.5, should be installed before 11.3.6.

If you've tried the Entourage 11.3.6 if it fixes (or causes) and problems, such as those listed on our Entourage/Exchange Tips and Reports page.

Office/Entourage 11.3.5 update focuses on security. May 9, 2007 -- Yesterday, Microsoft released Office 2004 for Mac 11.3.5 Update, a free download that adds security fixes for Entourage, Word, Excel, and PowerPoint. Microsoft describes the fix:

This update contains sevesral improvements to enhance security and stability, including fixes for vulnerabilities that an attacker can use to overwrite the contents of your computer's memory with malicious code. In addition, this update includes all the improvements released in all previous Office 2004 updates.

The developer of E2sync said yesterday that Entourage 11.3.5 also includes changes to its sync services that improve syncing. E2sync is a utility that can sync Entourage with iSync, moving Entourage contacts, calendar items and tasks to over 60 cell phone models, iPods and PDAs, and to iCal, AddressBook, and .Mac.

If you’ve seen the update positively or negatively effect Entourage and Exchange Server

Office 2004 11.3.4 security update released. March 5, 2007 -- Microsoft last month released security update 11.3.4 for Office 2004, including Entourage, version 11.3.4. Microsoft describes it:

This update contains several improvements to enhance security and stability, including fixes for vulnerabilities that an attacker can use to overwrite the contents of your computer's memory with malicious code.

Microsoft releases Office 2004 Update 11.2.4. June 14, 2006 -- Yesterday, Microsoft released Office 2004 for Mac Update 11.2.4. The update includes security improvements as well as other types of fixes for Entourage 2004 and PowerPoint 2004.

Microsoft warns that this update could cause data loss in certain situations with Entourage SP2 11.2.0. The website suggests some measures to take to prevent this problem.

( if this update addresses some of the recent problems we’ve reported on our Entourage/Exchange reports page.)

A Microsoft spokesperson also said that the company will be releasing two more updates over the next month: Office 2004 Update 11.2.5 and, for the older version of Office, Office X Update 10.1.7.

Version 2 of Exchange KB 911829 update may fix the Entourage problems. June 5, 2006 -- Microsoft has issued Version 2 of the KB 911829 patch for Exchange Server. The first version of the KB 911829 patch caused a problem with Entourage where users can’t see updates to recurring calendar events. It also causes a problem where Entourage users receive blank email messages.

Office 11.2.3 Update adds Entourage Sync Services.March 15, 2006 -- Microsoft released Office 2004 for Mac 11.2.3, an update to the suite for Mac OS X. The update features improvements to Entourage and to Messenger for Mac. New features in Entourage include:

Messenger for Mac 5.1 improves use with Live Communications Server, including:

MS Office 11.2.1 patch aimed at fixing Entourage SP2. October 21, 2005 -- Yesterday, Microsoft released Office 2004 for Mac 11.2.1 Update to fix problems with the recently released Entourage SP2, which we've previously reported. Microsoft "strongly recommends" that all Entourage SP2 users install the new update.

The company said that the 11.2.1 Update fixes a bug that could cause data loss when Entourage SP2 tries to synchronize with an Exchange mailbox that was moved to a different Exchange server. It also fixes problems with setting Exchange server permissions and with printing calendars.

Office 2004 SP2 fills holes in Entourage/Exchange functionality; Server patch also issed. September 23, 2005 -- Office 2004 Service Pack 2 for Mac OS X, a free update, focuses on improving Entourage's functionality as an Exchange client. Microsoft also issued an update for Exchange Server to support Entourage. Word, Excel, and PowerPoint received bug fixes and minor improvements. Among the improvement in Entourage 2004 SP2:

See this eWeek report for more.

March 29, 2005 -- Microsoft has posted the .PST Import Tool for Entourage 2004 as a free download. The PST Import Tool helps users more migrate data from Outlook 2001 for Mac to Entourage 2004. Microsoft first announced the tool in January.

Office 10.1.5 update. Released on September 3, 2003, the Microsoft Office v. X 10.1.5 Update "addresses several stability issues with PowerPoint®, Excel, and Visual Basic for Applications for Office v. X."

Microsoft Exchange Update for Entourage X (Office v. X 10.1.4 Update). Released August 4, 2003, this the official name of the first Entourage version to act as client for Exchange Server. The 10.1.4 update is free from Microsoft, 28.6 MB in size. The update has several requirements:

The Exchange features added to Entourage 10.1.4 include:

The biggest change from Outlook is that Entourage X v10.1.4 does not support the native Exchange MAPI protocol for calendar and address book connectivity. The MAPI protocol is used by the Exchange for calendar and address book functions in Outlook for Windows and in Outlook 2001 for Mac OS 9. Entourage X v10.1.4 instead it uses the WebDAV protocol, based on html. When the update was released, we asked Microsoft about it the lack of MAPI in Entourage, and received this reply:

This version of Exchange does not support MAPI. Through working with our customers and the Exchange team, we determined that adding calendar and address book support through WebDAV was the most efficient and timely way to meet our customers' needs. Entourage X supports IMAP protocol for accessing email from the Exchange server and will continue this support.

In addition, Microsoft said that the upgrade has other benefits not related to Exchange Server. From the Microsoft web site:

As an added benefit, all Office X for Mac customers should download this free update (even if they don't get their e-mail from an Exchange Server) to experience enhancements to Word X, PowerPoint X and Excel X.

Reader Reports

Topics include:

Reader reviews--Lack of MAPI support and other features found in Outlook 2001

The lack of MAPI support in the Microsoft Exchange Update for Entourage X is an important issue for many readers. The MAPI protocol is used by the Exchange for calendar and address book functions in Outlook for Windows and in Outlook 2001 for Mac OS 9. A number of readers also complained about the lack of MAPI and other features found in Outlook 2001. Other readers were more optimistic, noting the positive aspects of the new version, and hoping that Microsoft will build on these in a future release.

August 6, 2003
Brian Little explains why some sites need MAPI support :

I just want to emphasize to Microsoft that this is _not_ an appropriate tool for the enterprise. It requires IMAP, and does not speak Microsoft's proprietary MAPI protocol, as required by many server admins who refuse to enable POP or IMAP. Further, the address-book-via-LDAP scheme is useless to those of us without a usable LDAP setup.

In short, this "upgrade" makes a lot of invalid assumptions about what the end user is going to be getting from the back end ... Until we get MAPI, at the very least, we're stuck with 2001.

August 6, 2003
John Lockwood points out some of the features lacking in the new Entourage:

For those who don't know, Entourage X 10.1.4 is _not_ a MAPI client (like Outlook for Windows or even Outlook 2001 for Mac OS 9). Entourage X 10.1.4 instead relies heavily on using OWA (Outlook Web Access) -- this is definite ... This fact by itself would not be enough to condemn this application but it is certainly a bad start. None of the reports I have seen indicate ANYONE has successfully been able to use the Calendar feature.

Furthermore, Entourage X 10.1.4 has only a fraction of the features of Outlook 2001 (for Mac OS 9) which in turn only has a fraction of the features of Outlook for Windows.

Critical features that appear to be missing include (but not limited to):

  • .PST file support,
  • Archiving support,
  • Shared mailboxes.

Does anyone know if Entourage X 10.1.4 copes with TNEF attachments (from Outlook for Windows clients, also known as the dreaded WINMAIL.DAT problem)?

August 6, 2003
Dr. Michael J. Modesitt also notes the lack of features, but is less pessimistic:

I have noticed several problems for what should be referred to as a beta program:
  1. There are no delegation capabilities
  2. Tasks do not synchronize (entourage to exchange)
  3. Importing holidays cause major problems with syncing calendars
  4. Calendar synchronizing is typically delayed many minutes
  5. Calendar items that are dragged from one date to another do not sync properly; however you can edit the date and time manually, save it and it gets sync'd.

On the other hand, once I sorted out my server addresses for email/calendar (IMAP) and the busy/free server/directory. I could sync with my Palm, Entourage and Exchange server successfully. I could also busy search attendees for meeting requests. This is a good start.

August 6, 2003
Jon Armstrong:

The upgrade is nothing more than using IMAP to get access to Exchange. If your admins don't feel like implementing IMAP, you are screwed.

Like previous posters, my feelings are that this isn't a true Exchange client. If you had IMAP activated on your Exchange server, the previous version of Entourage would work to get messages. This seems to be a case of marketing selling something that doesn't really exist: A true Mac OS X Exchange client.

I wrote a rant at Blurbomat. After 2.5 hours of trying to get it to work, I gave up and used a PII laptop and Microsoft's Remote Desktop Connection tool to control the laptop via OS X.

August 6, 2003
Michael Morris:

Entourage for Exchange is an incomplete solution. It is not what it was hyped it to be. Our Exchange servers only support the MAPI protocol and since EDS runs things, they refuse to support anything else. I'm still stuck with Outlook 2001...

August 7, 2003
Tom Hesser is more optimistic:

I have been eagerly awaiting the 'so-called' Exchange compliant version of Entourage. While the 10.1.4 update would be an adequate short term measure, it really is not appropriate for use at a large company that is making full use of Exchange's features in a mixed platform environment. I have been following the thread on MacWindows about this and I fall somewhere in the middle on the opinion board. I agree this is not a true Enterprise solution in it's current form, and seems to indicate in Entourage Help that it only synchronizes "local" or "top-level" items.

"Only Calendar items stored in the top level of your Outlook Calendar folder are synchronized. Calendar items stored in subfolders or anywhere else are not synchronized."

The company I work for makes extensive use of public/shared calendars. While I had NO problems connecting to and synchronizing my mail, contacts, and PERSONAL calendar with our Exchange server, there is no way to look at public calendars. I can look at Exchange Public Folders, and I "see" the public calendars, but Entourage will display events as simply a list of email messages. This was a key feature we need here to consolidate our calendaring between Macs and PCs on Os X. Now we are stuck using Classic (2001) which lacks MANY modern email features.

So, it IS a step in the right direction, and worked fine during my setup (I am in charge of testing Outlook on the Mac...among other things). We are having trouble with LDAP in OS X apps, so getting the addresses from Exchange helps, and well as migrating personal address books. We are already using IMAP on Exchange, but we would prefer MAPI. It doesn't meet our large scale needs right now, but maybe the MBU is still working on better integration.

As for Palm Desktop, the update did not seem to affect the Handspring version of Palm Desktop 4.0 on my machine.

August 7, 2003
Jonathan Shmoolie:

[Exchange X 10.1.4] won't work for our company and I suspect it won't work for many more company's like ours. First of all it is not a real Exchange client. It doesn't provide full-time connectivity to the Exchange server, does not allow for access to pst files (very, very important), or to public folders. It won't work with Exchange 5.5 - it requires 2000 or 2003 both of which require Active Directory.

We need a real OS X Exchange client from Microsoft so that our hundreds of Mac users can keep pace with our thousands of Windows users. I hope that someone at Microsoft is listening.

August 7, 2003
Marc Hamilton:

Like many others I waited with cheerful anticipation for the arrival of the Entourage X Exchange update. The absolute most important feature I need is the Calendar syncing. Shame on Microsoft for being so disingenuous toward the Mac community. It was back to Outlook 2001, the last OS 9 holdout since I migrated to Quark 6.0. I remain hopeful that there will be a fix to MAPI support issue.

August 8, 2003
Susan Patton sent us a detailed review of the new Exchange client:

I have been using Entourage 10.1.4 since Monday. I am trying to have a positive attitude towards its shortcomings compared to Outlook 2001. However, I am not sure that Entourage is going to be a viable solution in our corporate environment. There are some things I'm happy to see.

We have over 100 Mac users and we are about 75 percent migrated to OS X. I am evaluating the features of Entourage 10.1.4 to determine what is different or missing so that we can make a decision about whether this solution will work for us or if we are better sticking with Outlook 2001.

On the positive side obviously it is nice to be able to abandon Classic. I'm delighted to be able to read HTML messages. I do not seem to be having the same calendar issues others have reported.

Shortcomings in my opinion are many. They include:

-- Lack of MAPI support. This is obviously not a true Exchange client. The first time a folder or the In Box is accessed it has to sync. This can take a considerable length of time. For the end user this will be unacceptable.

-- Lack of .pst support. I moved my own personal folders to folders in "On My Computer". I don't have all that many messages in the .pst file and it took FOREVER. I had to first move each folder of messages from my .pst file into my Outlook In Box then Receive a Complete Folder List in Entourage. Next I had to go into each folder moved to the In Box and wait for the messages to sync. It took a LONG time for each folder to sync, especially for messages with attachments. Then I could move the folder to my On My Computer folder. Lastly I had to go back into Outlook and delete the folder I had moved from my .pst file. At any rate the thought of performing this task on 100+ Outlook 2001 users is daunting to say the least. Many of these users have huge numbers of messages in personal folders.

-- Although I can set up a second account to be able to see another user's In Box I have to set up a second identity and switch identities to be able to see the other mailbox calendar. We have a number of Administrative Assistants using Macs who manage their bosses calendars. This will be an issue.

-- I haven't figured out how to get a Read Receipt for read mail. A number of people use this feature religiously.

-- I can search the Global Address List but not browse it.

-- Entourage seems slow to respond to typing.

-- There are Rules but no Out of Office wizard.

There may be other issues that I haven't found yet. Overall I'm disappointed with what Microsoft has given us in this release. But as I said I'm trying to look for the positives and to determine if there are work arounds or solutions to the issues I've identified so far.

Top of Page

Requires Exchange 2002 SP 2 or later--won't work with v5.5

August 5, 2003
Todd Barber verifies that the new Entourage does not work with Exchange Server 5.5:

I installed it anyway and I can only retrieve my mail (Exchange 5.5), I can not send it. Entourage was designed for POP mail and therefore it downloads all of your mail to a local database file (your mail and calendar records). This has not changed with the update. The records for Exchange (email, calendar entries,etc.) must be downloaded to your local Entourage database in order to view them. Then there is a synchronization that takes place to see if your local records match the Exchange server.

Entourage was never designed as an Exchange server client and it's still not. If you are just sitting there in you inbox you're not going to see your new mail instantly, only when it decides to try to synchronize on it's own or when you click the Send and Receive mail button.

September 23, 2003
Michael Backlund

Went to your page last night and saw a report that said Entourage X 10.1.5 won't work with Exchange 5.5 ... I am composing this email with just that configuration. I have applied Service Pack 4 to my Exchange Server and I have updated Entourage to version 10.1.5 so the user who posted the incompatibility may wish to try applying the patch to his Exchange server.

Backlund didn't mention if he can use any calendar functions.

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Problems with calendaring, suggestions for getting it working

August 5, 2003
Evan Williams can't get calendaring to work:

I've read through all of the MS docs on how to configure Entourage to work with an Exchange server and I still can't get the calendaring to work (Free/Busy data not found, error -3170 OR error -3248). Sending and receiving mail works, Public Folders are visible, I can search the Global Address List through the LDAP service, but no calendar.

We are running MS Exchange 2000 SP2. We meet all of the MS requirements for Entourage to work with the server (IMAP4, SMTP, Outlook Web Access--OWA, and LDAP are all running on the server) so I'm not sure what it is.

I've tried reducing the authentication settings to the lowest possible thinking maybe it was a SSL/authentication problem, I've compared all the port/security settings between the Entourage client and the Exchange 2k System Manager and they all match up.

Anyone have any ideas? The only thing I can think of is that we ran the MS IIS Lockdown tool and maybe that disabled some part of the WebDAV protocol that the Entourage calendar needs. Can anyone confirm this? Also, the error -3170 occurs if I'm trying to invite someone w/ an Exchange mailbox to a meeting, the error -3248 is if I'm trying to invite someone with an outside email address. But this isn't even consistent.

August 5, 2003
Brennan Pang can't book resources:

I've tried the new Office/Entourage update and it seems to work decently with our Exchange 2000 server but I have yet to figure out a way to book resources. We use resource booking to book all of our conference rooms when we create a meeting request in Outlook on Windows or Outlook 2001 Mac. This functionality is critical and doesn't appear to be enabled by this update. I'd love to know if any readers have figured this out. I hope I'm just overlooking something here.

August 6, 2003
David Rienzo:

I'm also having a similar problem with the new Entourage. Email works absolutely perfectly, and I'm able to access all the folders I've created using Outlook for the PC. When I use Entourage, though, I am unable to synch my calendar or contacts with the Exchange server. They do show up as folder items, however, in the sidebar.

We are running Exchange 2k, SP3 installed, OWA is enabled. I don't know if webDAV is enabled.

August 7, 2003
Evan Mati:

We have Exchange and the new update allows us to receive email but not send it. I have tried to set it up different ways and also just like our Windows clients.

I guess I'll have to wait for Panther's Mail Exchange implementation.

Microsoft should give us a better solution. I paid more for my New Office v.X then I paid for my Dell.

Suggestions for getting Entourage working with Exchange

August 6, 2003
Barry Shapiro has a suggestion for people having problems:

Installed the update Monday. We just got it working now. There were some initial problems setting up my account. These all seamed to point to some settings on the server side. If you have problems I suggest trying a temp user on the exchange server to debug possible errors on the windows side.

Once these problems were corrected every thing seams to work OK. There are some differences in the way things are done in Entourage compared to Outlook that you need to get used to. I found that you need to set the rules for send and receive mail to a schedule or time interval if you want your mail current. Otherwise the default is to manually send and receive. My contacts show up but I don't yet know how to add or edit them.

Overall this appears to be a much improved Mail application compared to Outlook 2001 which would not render images and or work with hot links in a message.

August 7, 2003
Sebastian Wohlrapp sent in some advice for configuring shared calendars with the new Exchange-enabled Entourage released this week:

The settings for participating in shared calendars are a bit tricky compared to the ones on the windows world client Outlook. If you do not use an external free/busy-server or -service set the string for free/busy-server to



/public/ seems to be the default location but might vary depending on the settings your admin will know about.

With this, Entourage becomes a fully usable Outlook substitute and relieves me from having to work with Windows.

Problem also occurs with the 11.2.3 Update

March 23, 2006
Frederic Boldireff Vauhallan in France

I have this problem of the error message "A secure connection cannot be established because the correct root certificate is not installed" appearing in Entourage (11.2.3) when I try to connect to the Exchange server of my employer. This problem appeared with the recent upgrade of their Exchange server. They used to run Exchange Server 5.5; it is now Outlook Web Access (or Exchange Server 6.5). I have contacted the IT department, but they are not willing to help. I have tried all possible tricks, but no joy. It seems I would need to provide Keychain with a Personal Information Exchange certificate (.pfx) that my IT department will not give away.

If you've seen this problem

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Problems with Active Directory

August 8, 2003
Will Jorgensen mentions a problem with Activity directory, and a problem with duplicate messages:

Here are some problems I've notices with the Entourage 10.1.4 update.

The first reason why this shouldn't have been released yet is the fact that it locks my Active Directory account out after one bad attempt. It apparently tries your password a number of times (>5 cause that is how many bad attempts we get before getting locked out).

Another problem which is mostly just annoying is that every new message seems to come to my mailbox twice. I do have rules that were set up using outlook on windows that could have something to do with it but it is annoying. The fact that it can't find our free busy server is going to make it a nightmare to support for our Mac users. However I think the entourage update is the right first step. It turns out that the new version of outlook will be dropping support for MAPI as well and it will essentially work on a local copy of the emails. It will however act like MAPI in that it will pull a message down as soon as it comes to the mailbox.

I think Entourage was written the way it was so that in the future it will work better even though for now it has many drawbacks. I encourage every one to contact Microsoft about their issues so that they understand how many of us need things like personal folder support and group mailboxes.

If you've seen these problems, please let us know.

Top of Page

Entourage 10.1.4 update affects Word, PowerPoint.

As was mentioned above, the Entourage X 10.1.4 update also made some changes to other Office applications. Readers have reported the update causing problems with

Problems opening Word 10.1.4

August 18, 2003
Michael Wilmar finds Word files are no longer double-clickable:

Since I downloaded the most recent update of Word with Entourage for Exchange Server, I find that, from time to time, I cannot open Word documents created in WinWord except from within Word. In other words, double clicking on the icon doesn't open the document.

August 18, 2003
Don Crowell also has a Word problem:

I installed the update, and now I can't get Word to open. Excel and PowerPoint open fine, but Word gives a message that Word has unexpectedly ended.

August 21, 2003
Bruce Bowden confirms the problem of double-clicking Word files:

I was also having a problem with double-clicking on Word files. Nothing would happen except that Word became the active application. I had to go to Word's File menu to open the document. This only happened when Word was already running. If Word wasn't running double-clicking on a Word document always worked.

This was happening before the office 10.1.4 update while running Mac OS 10.2.6. Since then I have had to reinstall my system and drop back to 10.2.4. Word has behaved itself since both before and after the Office 10.1.4 update, probably due to the system reinstall rather than particular system versions.

PowerPoint 10.1.4 Problems

August 18, 2003
Rich Tanksley has seen multiple instances of PowerPoint problems:

We've got a few clients that updated Office X to 10.1.4 so they could use Entourage. 10.1.4 includes some fixes to PowerPoint also. Since the update, PowerPoint crashes often. Just locks up with a spinning color wheel.

You can duplicate the problem by opening a new document, inserting a picture as a background. Putting an image on top of it, then going back and changing the background to the green marble background included with PowerPoint.

This locks up two different machines with the 10.1.4 update. Before the update, they worked fine.

We have reinstalled Office, trashed the prefs, etc.

August 21, 2003
Richard Rodriguez is seeing a problem with PowerPoint quitting:

I too am having problems with PowerPoint. Although it doesn't lock up like some of the other readers describe, it unexpectedly quits on me. I haven't been able to duplicate the problem, but it seems to be similar to what others have described after choosing a background. A couple of times, the first background selection caused it to quit, while other times it quits after adding a new slide.

One of the reasons I switched to Mac was because of so many problems with Windows, and MS Office for Windows. Now, I'm wishing that I hadn't bought Office for Mac.

If you've seen any of these problems, please let us know.

Suggestions of auto-quitting problems

August 21, 2003
Patrick Ellis has a general suggestion:

I count myself lucky that I have not experienced the crashes in Office following the application of the 10.1.4 update. I did, however, experience regular "the application has unexpectedly quit" errors with Office prior to updating. I ran fsck but no problems were reported. Reinstalling the package and trashing the personal preferences didn't help.

That being said, my crashes were resolved after trashing the Microsoft User Data folder that resides inside the Documents folder of my home library. I can't say for sure that this will resolve your readers' issues that occurred following the update but trashing the user preferences and this specific folder may be worth a try.

August 21, 2003
Andrew Hendrycks also has a suggestion for dealing with these problems:

I am not saying this is in any way related to the issues that some are having with Office apps crashing or even failing to launch at all.

But, what I have worked with on a constant basis as a System Administrator for 10 years is that fonts cause the most amount of grief. At the first sign of major application issues I go directly to my font folder(s) and check the Creation Date of all fonts.

As a general rule I will remove any font over 4-5 years old and then check the apps again.

Microsoft has many times in the past been one of the most stringent in regards to having their apps "check" fonts at launch time. If it finds any it doesn't like it tends to "crash". I wish they would offer a better error message than that, but hey Ö what can you do.

People should check their fonts on a more regular basis as old fonts WILL cause major system headaches. It may also directly help these Office issues.

Excel 10.1.4 Problems

August 21, 2003
A reader (who did not give his name) reports this issue with Excel:

Copying from Excel and pasting in causes both applications to hang with the spinning beach ball.

Problem quitting Office apps

August 21, 2003
Xavier Jubier reports a problem with all Office apps:

Since I updated, when I try to quit any of the MS Office apps I get the spinning wheel. The only way to quit is to do a force quit!

If you've seen these problems with 10.1.4, please let us know.

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Office X 10.1.4 update affects LDAP in Entourage

Readers are reporting problems with the recent Entourage 10.1.4 update and LDAP.

August 25, 2003
John Lockwood

It looks like Microsoft has made a major change to LDAP support in Entourage with the recent 10.1.4 update to Microsoft Office X.

I can now no longer access the LDAP server I used to be able to from within Entourage but CAN from Apple Mail (on the same computer). Note: the previous versions of Entourage X also worked (with exactly the same settings).

These and other tests lead me to conclude that Entourage 10.1.4 now only supports LDAP version 3 servers and not LDAP version 2.

Unfortunately, the LDAP server I am currently using is only version 2 and Entourage does not give any option to configure which version it should use (some other LDAP utilities e.g. LDapper can do both).

As far as I can see Microsoft have NOT documented this change!!!

While I can see why version 3 support has been added to Entourage (to better support Exchange servers) it is inexcusable for them to remove version 2 support especially without telling people!

August 25, 2003
Jeff Weitzman sees another symptom of "broken" LDAP:

So far I've not had many problems with the Exchange for Entourage update (other than being disappointed that the Mail protocol is still only cumbersome IMAP), but one thing is weird: The email addresses of employees in our LDAP server come through wrong. For example, an entry for Bob Jones with email address is often inserted into the To: field as We're using Exchange 2000.

August 28, 2003
Paul Bielski reports

I have a similar situation to what John Lockwood is reporting. It appears that if Exchange support is enabled, Entourage always attempts to authenticate to the Exchange LDAP server even if it does not require authentication. I have set up a separate non-authenticated LDAP entry for our Exchange server in Entourage, and I can successfully search the global list through that Directory Services entry (in Tools->Directory Services).

The really bad part is that using "Check names" when addressing a message apparently always checks the LDAP server defined by the Exchange support, yielding the error message "Directory server denied access." The "Check names" function will properly work if Exchange support is disabled, since the second non-authenticated LDAP server entry does work. Unfortunately, there is no way to disable the LDAP lookup associated with the Exchange support without disabling all of the Exchange support.

August 28, 2003
Evan Williams

I emailed you guys shortly after the release of the Exchange update for Entourage and have had some progress. Mail, Calendar, and Contacts now work okay (I had some SSL settings wrong) but checking Free/Busy meeting data still fails along with pulling email addresses from the GAL. It's the same problem as Jeff--when I type in a user that's in the GAL it will simply transplant the user's full name in front of our domain ending (i.e. - selecting Evan Williams from the GAL comes up with the email address, while it should be

I'm wondering if the GAL email address problem is related to the Free/Busy server not working correctly? I'm using the recommended settings for the Free/Busy server (servername-ip/public/) and that seems to fix it for most people. Maybe when trying to receive the Free/Busy data for someone it looks up the wrong username (EvanWilliams instead of ewilliams) just like when using the GAL?

10.1.5 doesn't solve the problem

September 8, 2003
John Lockwood

The recent 10.1.5 update did not restore the ability to search LDAP version 2 servers (i.e. you still cannot, whereas 10.1.3 and earlier could). Indeed after installing the Office v.X 10.1.5 update the Entouragte application remains unchanged at version 10.1.4 so this is not suprising.

A solution

July 2, 2004
Igor Portnoy send us a solution to the problem with Entourage 10.1.5 connecting to LDAP in Microsoft Active Directory with and pulling user's names and e-mail addresses

In order to be able to search Global List in Active Directory running on Windows 2000 Server with MS Exchange 2000 (haven't checked Windows/Exchange 2003 yet) by clicking on "Check Names" in Entourage X (10.1.5) when composing a new e-mail message, do the following:

1. Go to Tools --> Accounts --> Directory Service

2. Click on "XXX Exchange Account" and then click "Edit"

3. Go to "Directory"

4. In the "Search Base" field type dc=yourserver,dc=com (you can even specify users container by doing cn=users,dc=yourserver,dc=com)

5. Click "OK" and then "X" to close "Accounts".

6.Click "New"

7. In the "To:" field type a couple of letters of the person's name or e-mail address and click on "Check Names"

8. The list with names of people that you have recently sent e-mails to as well as list of people from your AD should appear.

Top of Page

Entourage an other don't start in Update 10.1.5

September 8, 2003
Paul Reading

I installed the 10.1.5 upgrade and Word, PowerPoint and Excel all refused to start, Entourage was ok. The all froze during the splash-screen display of loading modules. I called MS Support and together we trashed the "Carbon Registration" preference in the user Library/ Preferences/Microsoft directory. That solved the problem.

September 11, 2003
A reader named Dorian describes another problem with the recent Office X 10.1.5 update:

On a PowerBook 400 Ti, after going thru all the updaters, nothing but Word will launch. I had tried trashing all of MS's prefs and the problem persisted, I just tried your suggestion, which actually I had done by trashing the entire MS folder in the prefs, and the same results. Excel actually booted originally, but stopped as well.

Today I trashed the as well as, LSApplications, LSClamedTypes, and LSSchemes. It did not work. I will have to reinstall Office and if that doesn't work, I will have to reinstall OS X.

September 23, 2003

Office v.X running at 10.1.3. Installed 10.1.4 and 10.1.5 then installed each. Now Excel and Power Point Crash after the splash screen. You can see the Excel and Power Point menus briefly before it crashes. I've tried:
  • Rebooting
  • First Aid to repair permissions
  • Unchecking the "gallery" option in Word
  • Reinstalling 10.1.5

Still doesn't fix it.


September 26, 2003
Barry Shapiro

Another possible cause for Office apps to quit on start up is font conflicts. We had this problem while running FontReserve. The fix was to turn off Font Reserve before launching Office. I did not take the time to find the offending font. This problem is noted on Mactopia. It can also prevent the installers from running correctly.

Please note that it is almost never necessary to reinstall system software and very time consuming. The core system files are well protected as applications (for the most part) do not install items in the system directory. The Console app should show something to clue in to what has gone wrong.

If you've seen these problems, please let us know.

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Password problems with Entourage and Exchange

January 2, 2004
Patrick Centurion describes another problem with using Entourage as and Exchange client:

AD & Entourage -- what a farce.

We are running Active Directory with Windows 2000 servers and Exchange 2000 as well. Our Mac clients are 10.2.6 and are running Office 10.1.5.

The Password works well for the first month, when it expires and its time to change you start to get locked out. We have tried setting it up in different ways and also disabling any Keychain related passwords or activity. Still occurs on multiple machines.

We are now running Outlook 2001 with no problems, until MS pulls its hand out and gets a proper MAPI client for OS X.

January 2, 2004
Scott Daniels reports a similar problem:

I use Mail (having tried and dumped Entourage), but my password problem occurs from iSync. The password for syncing to exchange is not accepted. I've tried everything I can think of to get around it, but when the required password change occurred last time, the new one was no longer recognized.

January 6, 2004
David Glue

I am a Mac admit here who also experiences the Entourage password problem. One mistyped password, and poof! Account locked out. We're stuck using Outlook 2001 until this is resolved. Aside from missing some public folders, I can configure Entourage to work just fine within our AD domain, so this is particularly frustrating.

Using OS X 10.3.2, btw.

If you've seen these password problems, please let us know.


January 5, 2004
Mike Lincoln

This may not be the problem Patrick Centurion experienced, but if you try to change your password when more than one machine (e.g., your PowerBook and a desktop PC) are both logged in, then you'll get locked out. The same occurs if you're logged into two PCs at the same time.

January 5, 2004
Michael Greelish proposes a solution:

Yes, I have seen this problem. I am the IT Coordinator for eight OS X 10.2.8 Macs connected to a Windows Server 2003/Active Directory network. When we did NOT let Entourage add passwords to Keychain, users started getting locked out within 2 months of our OS X upgrade (from OS 9 with Services for Macintosh on NT 4 Server.) It didn't matter if there was NO Exchange password in Keychain (we even deleted the ENTIRE Keychain), or even if we deleted and recreated the entire Exchange user account in Entourage. What DID work is LETTING Entourage memorize user passwords into Keychain and then very carefully having IT staff delete the memorized password just a few minutes before changing the Windows network password on a PC (which is only way to do this using an AD network with 10.2.8--you can't change your Windows network password from a Mac in Jaguar.) Then, once the password is changed, we have IT staff carefully reenter it into Entourage, test it, and let it be memorized by Entourage via Keychain.

My theory is that somehow there is a "ghost" of the old Exchange password being retained somewhere, probably on the OS X client Macs. Entourage, if it has the wrong (or any) password memorized via Keychain, will resubmit it over and over in seconds if it's not accepted. This is probably to help in situations where the server is not responding, but WILL result in an INSTANT lockout if the password is wrong (or somehow has a "ghost" wrong password.)

I suggest others try our solution, come up with after weeks of agonizing with 3 other IT staff members during an epidemic of server lockouts. One poor guy was locked out every morning for three weeks until we came up with this solution. Fortunately, the solution has worked perfectly for the last 3+ weeks. Unfortunately we have no idea what will happen when we upgrade to 10.3 Panther by the end of February. Here's hoping Microsoft's new Entourage is out by then, or at least really soon after that, because the current 10.1.5 Entourage is a steaming pile we only use because Apple Mail's IMAP just couldn't cut it on the heavy email users' systems. BTW we can't seem to get Mail 10.3 to work with our Exchange Server 2000 either, but will upgrade to Server 2003 in February as well.

If you've tried this fix, please let us know.

Entourage bug and workaround

March 18, 2004 -- At first, Paul Levitt though that the Mac OS X 10.3.3 updated solved a problem with Entourage. He now believes that he has stumbled upon a bug and a workaround:

Ever since installing the Entourage for Exchange update, I've been unable to synch events originated in Entourage with Exchange/Outlook. I've exchanged many emails with a Microsoft MBU SW engineer, but everyone was stumped.

This is just too bizarre but, by accident, I think I found the bug.

I updated to 10.3.3 last night and, since it included many networking changes, I thought I'd try adding an event in Entourage to see if there was any improvement.

To my surprise, the new Entourage event immediately showed up in my Outlook calendar. I, of course, attributed this to 10.3.3 - but I was wrong.

Thinking the problem solved, I added another event in Entourage, only to find that it did not synch, and threw the same error I've been seeing all along. After comparing this event with the successful one, I noticed that the successful event included text in the description field at the bottom of the "New Event" window.

After some experimentation, I can now confirm that events generated in Entourage WiLL NOT synch to Exchange/Outlook unless text is entered in this field. No other changes had any effect. I have no idea whether 10.3.3 is a factor or not (it did solve some SMB issues).

Seems like a bug to me.

If you 've seen this problem, please let us know.

Entourage X problems with Exchange Server

March 30, 2004
April Acker reports four problems with implementing Entourage X with Exchange server on a large network:

I saw your Entourage for Exchange Special Report on and it struck a chord. I have been planning and implementing an OS X migration at a large corporation. The IT department wanted to integrate Active Directory and use Panther.

Anyway, everything has worked seamlessly except Entourage X which has presented a huge number of issues for users.

1. A problem with authentication causes AD accounts to lock out. There is no rhyme or reason to this.

2. Users occasionally cannot send mail, and receive an SMTP error which then also causes their AD account to lock out 50 percent of the time.

3. Some users can see public folders. Others cannot. Again, no rhyme or reason to this.

4. Some users cannot see updates to reoccurring calendar events, or when the update of the calendar event is sent, only the first instance of the reoccurring appointment is sent (i.e. if the event was first scheduled in 2001, this is the appointment that the user sees as an update!)

April 6, 2004
Sandra Ketrow verified one of the problem issues:

I just read April Acker's post about Entourage X problems with a large network, particularly the lockout issue. I have been totally stymied about this, thinking it was maybe OS X problem, maybe incompatibility with the network, but have not been able to find a fix. At least I know now what this is, and that I am not alone!

Suggested fixes and workarounds

April 6, 2004
John Bergh has some suggestions:

First, from April Acker:
1. A problem with authentication causes AD accounts to lock out. There is no rhyme or reason to this.

2. Users occasionally cannot send mail, and receive an SMTP error which then also causes their AD account to lock out 50 percent of the time.

I have noticed that if you configure your Entourage account as and "Exchange" account there is some sort of Microsoft voodoo with regards to the entering of your password. If you enter your password incorrectly it shows up as FOUR failed attempts on the Exchange server side... I don't know if that number is different in other organizations, but I'm an Exchange admin and I just saw it happen minutes ago. A similar situation exists with OS 9 and Outlook 2001. We just increased the "account lock" to 9 failed attempts and that helped our OS 9 users and their not-so-nimble fingers.

Related to this is yet more MS weirdness... You must type your password slowly or it will fail. If I recall you don't get an error (you get right in to Entourage).

Add this on top of it all: I can fail my login attempt but still receive mail... If I try to send mail I get prompted to reenter my password (because I flubbed it earlier) and then it works.

So, most of this can be alleviated by entering your password slowly. Don't ask me why!

I set up Entourage as an IMAP (not Exchange) client and I don't have either of those problems. I don't get calendaring but it's worth the decreased hassle. I also had to set up Directory Services separately to hit the "global" address book but that too is okay with me. There are other issues I'm slowly discovering so I'm recommending Entourage on X with certain reservations, to say the least.

April 12, 2004
David Morgenstern has a suggestion for the problem authentication causing Active Directory accounts to lock out:

I also have had much painful experience with this issue. Certainly, I've found that if there is any hint of an authentication problem then the account is locked out. This lockout happens even if I've only received one error message telling of a wrong password and I supposedly have a couple more tries in the bank. Nope. It's locked out on the first go.

Sometimes, I've noticed that the authentication problem is worse when moving Entourage from Offline mode back to Online. So I now do the following: Click Entourage into Online mode and then Quit the program. Launch the program and enter the password.

(Morgenstern is the West Coast editor of, and a contributing editor at Creativepro.) 

Jeff Boyle suggests reinstalling Office X:

We have been having intermittent problems and some major pains with Exchange and Entourage. I highly recommend the tips on the Entourage MVP site [part of the Microsoft MVPs program]. They suggested clean install of Office X (use remove Office if you have to which is on the value pack):
  1. Boot into safe mode (Shift at restart) and isolate the machine (i.e., no network or peripherals and stop all startup processes).
  2. Install Office X (I also put on most of the value pack including fonts) then open each app to initiate it.
  3. Then install the patches and again open each app.
  4. Repair disk permissions.
  5. Now configure Entourage manually for Exchange while in safe mode.

    Runs like a dream on three machines so far. Its a pain, but it works!

Entourage/Exchange calender problem

March 30, 2004
Ben Robertson has problems with calendars:

I actually decided to test this on my install of Entourage because I was having some trouble (more like oddities) w/ Outlook 2001, on Exchange 2000 with new G5 dual 2's (10.3.3)

I actually could see any calendar event that I create, and it shows up in my calendar, but there's no "accept", and the older calendar events that are already seen in Outlook, and which recur monthly, aren't seen in Entourage. Also, there's no way to specify which calendar event belongs to which email address (if you've got multiple accounts)

Also, the Address book doesn't seem to work. I don't get any of the global address' listed (but, they are seen because you can start to type a users' name, and it gets filled in)

If you've seen these problems, please let us know.


April 6, 2004
John Bergh has a suggestion for the address book problem:

If you go to Tools->Directory Services do you see them? Again, I've stopped using the "Exchange" account setup but I recall that my "global" addresses did not show up in my "Entourage" address book, only under Directory Services.

April 12, 2004
Eric Morgan

I recently upgraded servers from Windows 2000/Exchange 5.5 to Windows 2003/Exchange 2003. I spent a good part of the morning trying to get all features on Entourage (Mac OS X 10.3.3) working--global contact list, Calendar, scheduling, and email). I quickly discovered that you need LDAP&Free/Busy server configured to make this happen.

I wanted to make sure everyone knew about the "search base" option on the Directory tab. I put in the active directory tags (cn=users,dc=domain name,dc=com) in the search base field.

Users = user container name.

domain name = domain name - com = com.

In the Free/Busy server field I put the servername/public/.

I can now search my global contact list and schedule appoints with co-workers, calendar, and email.

Entourage/Exchange calendar gets erased; Getting Free/Busy to work

May 13, 2004
Robert Berger reports two problems with Entourage accessing Exchange Server. The first sounds serious:

1.) I've now had a repeating problem where my calendar items get completely wiped out periodically (and unpredictably). Usually, the items are still available in the Exchange Web interface, but sometimes, it will resync and put the items from Exchange back into Entourage. Most times, it just ends up wiping out the calendar in both places.

I have no idea how to track this down. Are there log files to look at? Is there any way to recover my calendar info (it wipes out EVERYTHING, my entire history).

2.) I also have not been able to get Free/Busy to work. The Entourage interface lets my check the free/busy status, gives me a login prompt to log into the Exchange web interface server. I don't know how it got the address of the web interface server as I entered the Exchange Server real address ( in the free/busy server field in the Advanced tab of the Accounts preferences.

After I click OK on the login I get:

Error: Scheduling data could not be found

Explanation: Scheduling data could not be found. Check your Entourage account settings and try again. If you continue to receive this message, contact your Exchange account administrator for assistance.

Error: 1401

I am running Windows 2003/Exchange 2003 on some HP server (its not under my control), Mac OS X 10.3.3, Microsoft Office v. X 10.1.5 on a PowerBook G4.

If you've seen either problem,

May 18, 2004
Pete Crosby reports seeing the first problem:

I have had the same problem and I have lost all of my calendar events several times. All I can recommend is that you back up your Microsoft Users Data folder frequently. At preset I am only syncing items from a specific category rather all.

I have had users that sync all categories and have not had problems.

May 18, 2004
Darren H. has also seen the loss of calendar events as well:

I have had this happen to us as well... Out of about 15 Macs that we have using Entourage with Exchange, 3 different users have had their calendars totally wiped out (one person in particular it has happened multiple times). Luckily we backup exchange mailboxes and were able to restore the calendar, but it's very annoying.

I am sure that we do not have virus scanning (or any other type of scanning) turned on for the M: drive. The calendar wipeout only happens with Entourage users, not with any of our PC users.

May 18, 2004
Karen Elsbree offers a suggestion for the Entourage Free/Busy problem:

We have also seen this problem with the Entourage Free/Busy. We have replicated the Free/Busy folder from our 5.5 sites to our 2003 site and used the FQDN/public/ in the free/busy server field and the error went away.

However, we still have "no data" for the calendars when we create a meeting and click on the scheduling tab.

May 24, 2004
Daniel Hudkins

We are using Exchange 2003. I am using OS X 10.3.3 and Entourage Version 10.1.4.

Today I experienced exactly the behavior described in the May 13, 2004 posting of Robert Berger. It deleted my entire calendar folder from the Exchange server. I had to restore from a backup.

I have taken Entourage (which I was testing for next academic year) offline and will not begin again until patch is available or we get 2004.

May 24, 2004
Lorin Rivers

My calendar and contacts also were deleted. Entourage got blamed for bringing down the Exchange server...

June 11, 2004
Jim Roletter

We had the same problem here with a user in our school district. He was using Entourage all his calendar items on the Exchange server were deleted. The connection to the Exchange Server was being made via IMAP over a network while at a conference.

July 15, 2004
Alexis Chen

I am having the very same problem. Folders of email and Calendar randomly disappears. Resync with the server, then the user works in and out of the office (connecting to the server in the exact same manner - I have the webmail alias for external use, mapped internally to our server through our DNS hosts file). Users have been up for approximately 1 month, then more consistently, 1 day before the next disappearance.

Specs: Windows 2000 SP3, Exchange 2000 SP3, Office 2004 (Entourage 2004), Panther

Suggestions for getting Free/Busy to work

May 26, 2004
Jeremy Reichmans

One of the people asking about Exchange was trying to get free/busy to work in Entourage 10.1.4/11. It will not necessarily work in the same server that you access your account from.

Entourage 10.1.4 and 11 both need access to the Public Folders server in order to see free/busy data. In my environment, we finally got this working for Entourage 10.1.4 and later by replicating the free/busy Public Folders from a back end server to all of our front end servers.

This is accomplished through an Exchange replication process, and I presume it's automatic. It means that we can type in the address for our front end server followed by "/public/" in the Advanced tab of the Exchange account setup, and free/busy will work.

This advice is now on the Entourage MVPs site.

We also require DAV over SSL, so the DAV connection to the free/busy Public Folders is also encrypted.

Also, since it's vaguely related: we could not get event invitations to be recognized as such in Outlook/Windows and OWA clients. They would show up as .ics attachments, not invitations (with the accept/decline interface). It turns out that, because we were asking Entourage 10.1.4 users to send out messages through our non-Exchange SMTP server (PMDF Mail), their invitations were not getting the required MAPI wrapper. I would suggest anyone who is having problems set up SMTP services on an Exchange server -- however, normal precautions apply, so you'll probably want to require authentication (Entourage 10.1.4 can use SPA, which I think is NTLMv1) and SSL.

March 29, 2005
Anthony DiPiano

I have a client using Entourage 2004 with Exchange and twice in the last 4 months, he's lost calendar entries. The first time it happened, I noticed that some entries were in the calendar. I think some of them were from when he was using Entourage X. Really strange. I haven't been to his site to evaluate the latest loss of entries, but expect that it will be similar to the last time.

Suggestion for loss of calendar

June 11, 2004
Todd Schneider has a suggestion that is a bit unexpected:

Does your Exchange Server have a drive letter "M"?

We had a similar problem with hot syncs to user's folders where the calendar would get wiped out. (Actually, all the calendar events would loose their start times and end up on the current day).

Turns out that every time a server virus scan ran it would scan drive 'M' and corrupt the calendars, after the next sync was done only users who synced their palm pilots were affected.

You may want to check your virus scan schedule to see if there a connection.

June 22, 2004
Darren H. replied to this suggestion:

I am sure that we do not have virus scanning (or any other type of scanning) turned on for the M: drive. The calendar wipeout only happens with Entourage users, not with any of our PC users.

If you've seen this suggestion work,

Entourage/Exchange email deletion problems, disappearing email

September 24, 2004
Jon Gardner

There have been reports of disappearing email when using Entourage X or 2004 with Exchange Server 2003. This sounds similar to the disappearing calendar problem reported at MacWindows.

We have experienced this problem as well. I've tossed it at our Microsoft Premier Support team to see if they can give me any constructive assistance; in the meantime, my recommendation is to stay away from Entourage altogether and use in conjunction with Snerdware's excellent integration tools for Exchange Server calendars and address books. Using ADmitMac helps too, but is not strictly necessary.

We've previously covered announcements of Snerdware's Address X and Groupcal. If you've had experience with using Snerdware's tools with Exchange Server, or have seen email disappearing

Office 2004 Issues

Microsoft has released Entourage 2004 as part of the new Office 2004. According to the Microsoft web site, it still requires WebDAV and LDAP to be enabled on Exchange Server 2000 (with Service Pack 2) or later. Our first reader reports on the new version were mixed.(If you'd like to comment on Entourage 2004, )

Readers find problems with Entourage 2004

A pair of reader found new problems that they say did not occur with previous versions of Entourage X.

May 24, 2004
Daniel Katz reported a problem with Entourage 2004 and Exchange receipts:

I have all my Exchange return receipts filed into a "receipts" folder, which has worked fine in Entourage v.X without a problem. However, I noticed an odd thing when upgrading to Entourage 2004: most of the contents of the "receipt" folder would not sync with Exchange! Strange is that some of the files did sync and always the same ones, even after recreating the Entourage profile or emptying the cache. These files are visible in Outlook 2003 and Entourage v.X -- why not Entourage 2004?

I've narrowed down the problem to this: Entourage will NOT see Outlook "Read" or "Not Read" receipts. It will, however, see Delivery ("Delivered") receipts. You can easily replicate this by sending yourself an e-mail using Outlook 2003, asking for both a Read and Delivery receipt. You will receive both receipts in Outlook 2003, but in Entourage 2004 you will only receive the Delivery receipt. I have duplicated this on more than one Entourage installation and Exchange account. We run Exchange 2003.

As far as I can tell, this is a MAJOR flaw in Exchange support for Entourage 2004 that did not exist in Entourage v.X's IMAP support.

May 24, 2004
Jeremy Matthews found several problems:

I imported settings from Entourage X, and I noticed a few problems that don't appear under Entourage v. X:

1) Using the "check names" LDAP lookup feature in new email returns a -17799 error: The directory service was unable to perform the search. Settings are identical in both versions of Entourage.

2) "Subscribing" to public folders does not include their children. If you want a subfolder, you have to select them one by one (what a pain). Also, Entourage says that there are no messages for some public folders, of which I find more than 200 in Entourage v. X and Apple's Mail!

Both versions are setup identically...

May 26, 2004
Richard Jenkins replies to Monday's report by Jeremy Matthews (directly above). He's seen both of the issues Matthews reported, but believe one of them is a feature, not a bug:

> Jeremy Matthews:

1) Using the "check names" LDAP lookup feature in new email returns a -17799 error...

That is our experience as well. We have Exchange 5.5 in production and Exchange 2003 in late testing, and various LDAP services on other platforms. We can't get LDAP info, using either identical settings or a variety of new configs. We'll keep trying though.

> Jeremy Matthews:

2) "Subscribing" to public folders does not include their children. If you want a subfolder, you have to select them one by one (what a pain). Also, Entourage says that there are no messages for some public folders, of which I find more than 200 in Entourage v. X and Apple's Mail!

No, this is a feature! We have thousands of the damn things on our server, and most other IMAP clients just grab the whole list. This is a huge time waster, as an initial connection has to download them all and their content headers, and then while you're subsequently connected it keeps sneaking looks to see if anything changed, and synchronizing them... I for one am glad to see some management of Public Folders in a Mac client.

Can't please everyone!

May 28, 2004
Adrian Cooke found that binding to Active Directory had a negative result on Entourage 2004:

I first tested Entourage 2004 Test Drive on a Mac with wasn't bound to AD with the ADPlugin. It found the Exchange 2000 server, directory server and free/busy server. Mail, calendar and contacts all synchronized okay, although they took a long while to do so, about 15 minutes for my mailbox which is 50 MB.

I then tested it again on another Mac which was bound to AD with the ADPlugin. This time it wouldn't find the directory server or free/busy server.

May 28, 2004
David Hulse found problems with signatures and OLE tables and images:

I've been using the Test Drive of Entourage in conjunction with Exchange 2000 servers. I'm pleasantly surprised about most of the features, but one thing I noticed was that email signatures appear to be either on for all mails or off. There is no equivalent of the Outlook for Windows option to discard the signature when replying.

An email with OLEd graphics such as a JPEG or a table directly sent from Word or Excel also will not render correctly in Entourage. If Microsoft could fix this one, the Entourage client would finally be able to replace the PC on my desk, which is currently there for Outlook only.

Readers with easy upgrade experiences

May 24, 2004
Rick Hazey reports success in getting Exchange 2004 up and running:

The Windows IT department of a client of mine received and installed Entourage 2004 on his MacOS X computer, but was unable to configure it properly for use with their Exchange Server. Having installed Entourage X with mixed success in the past, I wasn't too optimistic. However, much to my surprise, setup was fast, easy, and automatic. The setup consisted of allowing Entourage to locate and retrieve the configuration information. All I had to do was verify the information as correct.

I decided to try the test drive version with another client, where I had been unable to make Entourage X work at all. The process was also fast and automatic...This is a vast improvement over previous versions and I can finally rid my corporate clients of Outlook 2001.

May 24, 2004
Timothy Frantz also had good luck, using Entourage 2004 for Mac Test Drive:

Well, after a year or more of trying, I can now use one program for my email needs. Out of the box, Entourage 2004 imported my old Entourage X settings and I can now send email OUTSIDE of my company's Exchange network.

Before, I could send/receive email normally from coworkers, and I could receive email from outside the network, but I had to use the web-based client to send outside the network. What a pain it has been to have two programs open all the time. But this seems to be working fine.

May 28, 2004
Shane Palmer had a positive experience with Entourage 2004 and calendars and contacts:

My initial testing of connecting Entourage 2004 (I am currently using the Test Drive version) to Exchange is much more positive than that of Entourage X. For one thing I was not able to get Entourage X to work with my Exchange calendar and contacts, and although it works now in Entourage 2004 it could have also been fixed by the upgrade of our Outlook Web Access server to Exchange 2003. I have not done much testing beyond this though.

Readers with problems with upgrading

May 26, 2004
John Wilson found a problem with Entourage's installation:

I installed Office 2004 yesterday afternoon on my Mac, told the install wizard to import my previous identity (from Entourage) and then delete all previous versions of Office (which on my Mac went back to Office 98 in some esoteric settings in the Classic side). It seems to have done all that correctly. When I opened Entourage, it remembered all my settings, displayed my calendar, contacts and e-mail correctly. So far so good.

THEN I noticed that e-mail was disappearing from my Exchange Inbox and discovered that it was being moved to the LOCAL Inbox. As I kept watching, mail continued to be moved from my Exchange mailboxes to my local Inbox. Since I work in an IT dept., I thought I should let it go to see what happened for testing purposes. By this morning there were over 3700 e-mails in my local Inbox. I have a very extensive storage hierarchy on our Exchange server (several hundred folders?) and some e-mail from most of those folders has already been moved to the local Inbox. Most of those e-mails have an icon indicating that they are "on the server" (about 95 percent), but others indicate that they are stored locally. Looking at my Exchange account from Apple Mail, I see that the e-mail stored on my office Mac's local Inbox is not showing up in the folders they are supposed to be in, so to some degree or another they seem to have been truly moved (more than the 5% that don't have the "on the server" icon).

Additional info - I have no rules set up in Entourage at all. Junk mail is on, at the lowest setting, but that should move junk e-mail to the server Junk Mail folder, not the local Inbox. This may have been occurring in Entourage X as well. I hardly ever used it because I had been seeing some strange e-mail moving around, like the symptom described above.

Guesses at this point: Entourage may be trying to make a local copy in case it gets disconnected from the server -- an Off-line copy -- but since the folders don't exist locally, everything gets copied into the Inbox. Counter argument: all mail from the Sent Items were moved to the local Inbox, not the local Sent box, which does exist. (My server Sent box is now empty!) (Not sure if both Sent folders have the same name, however. Have to check.)

I quit Entourage so this anomalous process has stopped, but I now have to reclassify 3700 e-mails!

If any of you have ideas why this is occurring, please let me know. At this point I would say I can't recommend Entourage at all.

June 25, 2004
Jim Howard

I had a similar experience trying to test Entourage 2004 as reported earlier by John Wilson. Based on his experience, I did a clean install of Office 2004, manually configured (as much as possible in the Exchange environment) the setup, turned of everything that was automatic (or at least I thought ). Including junk, synchronization, etc. When I started it promptly still cycled through my entire exchange folder structure (about 4300 messages, in about 20 different folder/trees) and moved them all. If it had moved them to the local inbox I would have been okay with that. But it moved all messages from every server folder to the Deleted items folder! I manually copied them back to a new folder to hold them for resorting , but it moved those all to the deleted items folder also! So I quit Entourage 2004, went to my PC, and used Outlook to move the messages back to the inbox/other folders.

Needless to say this is not adequate behavior from a supposedly enterprise level product.

Word 2004 problems

May 26, 2004
Jardar Abrahamsen has a Word 2004 review that reports problems with compatibility with Word for Windows when certain international characters are used. He sent us a summary of his report:

  1. Problematic support for keyboard layouts.
  2. Improper input methods for "Unicode characters". The consequences are:
  3. Incompatibility with Word for Windows.
  4. Incompatibility with other Unicode-savvy Mac applications: copy and paste.
  5. Incompatibility with other Unicode-savvy Mac applications: save and load.

Entourage 2004 17799 LDAP error

May 24, 2004
Jeremy Matthews

I imported settings from Entourage X, and I noticed a few problems that don't appear under Entourage v. X:

Using the "check names" LDAP lookup feature in new email returns a -17799 error: The directory service was unable to perform the search. Settings are identical in both versions of Entourage.

May 26, 2004
Richard Jenkins 

That is our experience as well. We have Exchange 5.5 in production and Exchange 2003 in late testing, and various LDAP services on other platforms. We can't get LDAP info, using either identical settings or a variety of new configs. We'll keep trying though.

April 3, 2006
Julie Soucek

I was able to fix this problem in Entourage 2004 by removing the search base string (dc=company,dc=domain,dc=com) in the LDAP tab. This makes no sense incidentally, as earlier versions required this.

Also, adding my Exchange server in the "exclusions" list for our proxy eliminated the login errors that some users reported. (I've noticed that exclusions don't always work right away so be patient. Also, make sure to restart Entourage after each change that you make.)

TIP: Importing Address Book contacts into Entourage 2004

That is our experience as well. We have Exchange 5.5 in production and Exchange 2003 in late testing, and various LDAP services on other platforms. We can't get LDAP info, using either identical settings or a variety of new configs. We'll keep trying though.

May 26, 2004
A reader reports:

The new Entourage looks nice-and-neat, except for one BIG glitch: There is no way to import contacts from Apple's Address Book to Entourage's. This problem existed in Office X, but I thought they'd have thought of repairing it...

There's no way I'm going to manually rewrite all my contacts in Entourage, and just because of that glitch I'm not going to use Entourage...


May 28, 2004 -- Several readers wrote in response to reader complaint that Entourage 2004 cannot import Address Book contacts.

Eleni Nine sent us the names of a couple of utilities that fill some holes in the recently released Entourage 2004:

To the person who stated that Entourage 2004 does not provide a method to import Address Book contacts, I have a free solution (and good one at that). It's Address Book Exporter, a freeware solution that exports all your Address Book contacts to a tab-delimited text file. Even better, it provides settings specifically for matching Entourage (although it is for Entourage x.V, it still works very well w/Entourage 2004).(Be sure to give a small donation for your appreciation.)

As for synching the two programs, the best solution (although very complex in settings) is Sync Entourage-Address Book 2 which is designated for Entourage 2004 and Panther Mail. It's shareware that runs $20 but if you need to keep both apps synchronized then this is your best solution.

Rand Lien is using iSync:

It took a while and and new phone, but I've been successful at using iSync with Entourage 2004. It also synced all of my contacts from Apple's Address book (hundreds). First I installed Entourage and imported all my Mail settings and messages (thousands). It worked great, even kept all my folders intact. Then I purchased a new Treo 600 and set it up with iSync. Then I used PalmOne's HotSync Manager to sync my phone with Apple's Address Book and iCal. The combination of the Treo 600 Address Book and iCal sync with iSync, and the HotSync Manager sync with Entourage keeps all my tools (toys) in sync, including my Mac at home though .Mac with iSync.

MS can make life difficult, but I must admit that I love the new Project feature in Entourage 2004!

June 2, 2004
Dr. Ioh

You can also export all your contacts from Address Book as a single vCard, then drag this to Entourage's Address Book. Works well, with minimal cleanup.

Entourage 2004 not querying LDAP or AD.

There is one tip offered below.

(Also note that readers have reported LDAP problems with Entourage 10.1.4 and 10.1.5 and an Entourage 2004 17799 LDAP error.)

June 2, 2004
Martin Hill asks for help with this problem:

Entourage 2004 is unsuccessful in querying our LDAP server or our Active Directory Server to pull out addresses of users in our organization we wish to email to.

Apple's Address Book does successfully connect and query our LDAP server as does Apple Mail, but Entourage 2004 refuses to.

Test we have done so far indicate that Entourage is sending malformed LDAP queries that have the LDAP server sending back error messages. We've found that calling up Entourage's Directory Services and typing in the email address of someone in our organization WILL correctly pull up their entry in the LDAP server, but typing in their name doesn't work!

We'd be keen to know if anyone else is having problems with this as well or whether it is an issue with our particular configuration?

June 28, 2004
Gary Estler is another reader with this problem. He also reports other annoyances:

I'm running a Ti G4 PowerBook with Mac OS 10.3.4 and recently upgraded to Microsoft Office 2004. I was hoping it would allow me to finally cease reliance on Classic and Microsoft Outlook 2001 for my Company's Exchange Server based email. I got everything to work EXCEPT access the Global Access List.

I've used all the possible ways of inserting the server's address in the Directory Access option to no avail. The typical response I get is LDAP Server Error (-17768).

As frustrating as it is, this may be for the best as I find some of the limitations of Entourage to be quite annoying. For instance:

  • No ability to "Save As" from the Inbox message list view.
  • Messages must be saved as either text or Entourage Mail. (No option to save as .rtf or .htm).
  • No ability to customize the toolbar.
  • No "Save Attachments" option in the toolbar.

June 28, 2004
Casey McCullough

We are not even able to get Entourage to query Active Directory by email address. We keep getting an Error -3260 when we type in a name or email address in Directory Service. The Error -3260 description is as follows: "The connection to the server failed because the network is unavailable."

I'm able to send/receive email, so that's not the problem. I searched this error and came up with nothing.

I think I've got all the right information plugged in on the setup of the Directory Service, but any help/advice you could give would be greatly appreciated.

Suggestions for Entourage 2004 and directory services

June 25, 2004
April Acker

Several users in the group I support were recently upgraded to Entourage 2004, which works great with Exchange and seems to have solved the email-related lockout issues. However, one reoccurring issue we ran into was that Directory Services no longer worked for looking up contact information. Changing the LDAP server to an IP address didn't work either - in fact nothing seemed to work. At the root of the problem was the fact that I had imported the user's previous Entourage X identity. Something involved with importing the identity caused Directory Services to no longer work.

However, deleting the profile and re-creating it allows Directory Services with no problem. All the user's mail will have to be downloaded again, but it is a sure way to fix the problem. I still recommend importing the identity if elements such as signatures, rules, or archived local mail existed in Entourage X. After the import, just delete the actual Exchange profile and re-create it again, with all of the other elements in place already.

July 15, 2004
Jay Christianson found that the above fix worked

I read the fix for directory services that related to identities. I went into the File menu for Identities and switched identites, made a new identity, and yep the LDAP lookups work now.

July 15, 2004
Ernest Lehmann's and has another fix:

Like most other people who upgraded to Entourage 2004 with an Exchange 2000 email server, I found myself trying to figure out why I kept getting errors in LDAP queries after I'd upgraded.

I had to edit the directory services account (under the DIRECTORY tab).

And adjust the search base to read: dc=mydomain,dc=com

And I also had to check "This server requires me to log on"

I needed to ensure the following was unchecked: Override default LDAP port 389

July 15, 2004
Martin Hill has it working now, but isn't exactly sure why:

I previously reported problems getting Entourage 2004 successfully querying LDAP to auto-fill email addresses or even look up names in Directory Services.

This is now working for us and I suspect it is something to do with the LDAP server we have been using. Previously we were using the LDAP server running on our old Exchange 5.5 server as the new Exchange 2003 server refused to talk LDAP to our clients at that time.

However, after reports that some of my colleagues recently had success connecting to the new AD server, we tried again and it now works fine - autocompleting email addresses after clicking the "check names" button in email messages as well as searching on names in Directory Services.

We didn't have to delete identities and re-create profiles or anything. We also didn't have to enter anything into the search base field - we had previously experimented with this field (dc=yourserver,dc=com etc) without success and in the end it works for us with this field blank.

We did need to tick "This server requires me to log on" and "Override default LDAP port" and fill in the custom port number our Exchange sysadmins specified. (We had set these same options this previously with no success.)

July 27, 2004
Alan Klein passed a fix he found for a problem with Entourage 2004 and LDAP directory access that resulted in an error code 17799:

I'm the Mac consultant at a major corporation in New York City and once we upgraded to Office 2004 we could no longer get access to the Exchange Server's Global Address Book &emdash; which caused a major problem for our Mac users.

I stumbled across the Entourage 2004 public forum at Microsoft and came upon a fix that worked. Here it is:

Re: LDAP error code 17799
Date: 29 Jun 2004 21:48:10 -0700
From: Steve Gualandri
News Groups:

I recently upgraded to Office 2004. I was using Office X. I had no problems with Directory Services and other LDAP stuff in Office X.

Since upgrading to Office 2004, I am unable to perform an address lookup in Entourage 2004 V11.0.0 (040405). I continue to get "Directory Service was unable to perform the request Error 17799". I verified my settings and they are the same settings that I used in Office X. Can anyone tell me what error code 17799 is? I am running OS 10.3.4.


I actually talked to support about this one. In my case, it ended up being simple. Edit the Exchange Account Settings. Under the "Directory" tab, open up "Advanced Options". Make sure "This server requires me to log on".

By the way, I did not have that error code. My only symptom was failed searches in Entourage's Directory Services.

I checked "This server requires me to log on" and everything now works!

TIP for Entourage and Exchange Server 2003 disappearing folders.

July 15, 2004
David Pughe (of London) passed along a tip he found about folder names in Entourage:

Yesterday I found out that if a folder under your Exchange Server inbox has a forward slash (e.g. "books / CDs") then it will not show up in Entourage v.10.1.5. Remove the / and it shows up in Entourage.

Entourage 2004 support of global address lists without WebDAV

Michael Lincoln sent us two reports in July and September of 2004 on how to get an Exchange Server global address list (GAL) or distribution list into Entourage 2004, even if your system administrator won't turn on WebDAV in Exchange Server 2000 and later.

In Part 2 of Lincoln's report below, he describes how the solution he proposed in Part 1 in limited by the sparse display of global address list (GAL) data inside the Entourage GUI. He describes a workaround to that enables the full GAL to be displayed in Entourage. He also describes syncing to iCal using an AppleScript

Part 1

July 19, 2004
Michael Lincoln

At my organization has turned off WebDAV service in our Exchange 2000 servers. Our security office considers WebDAV to be a security risk. Before now I had continued to use Outlook 2001 (under Classic) because I needed the global address list (GAL).

I've now adopted Entourage 2004 and have my GAL despite lacking WebDAV. Apparently Entourage directory services do not depend on WebDAV, only the mail itself. I have therefore created two active Entourage accounts: an IMAP account ("VHA Mail") for mail, calendar events, etc, and an Exchange-type account ("VHA Directory") for directory services. The IMAP account is set to be the default for mail, but under the Directory tab the Exchange account is set as the default for directory services. Now I can "check names" against the GAL when (via "VHA Directory") when writing messages using "VHA Mail"! This provides 99 percent of the needed Exchange functionality: mail, calendaring, and directory services all work. Only public folders don't work: although the "VHA Directory" account shows the public folders icon, I can't see the mail inside because I lack WebDAV.

By trial and error I encountered a few settings tweaks that I seemed to require: I used the IP address of both the Exchange server and the LDAP server because name resolution didn't seem to work for the Exchange account (something to do with WebDAV?). In the Directory tab I also had to check two advanced options: "This server requires me to log in" and "Override default LDAP port (3268)". Finally, I used the schema "IP-number/public" for the free-busy server under the Advanced account setup tab. However, as mentioned above, I can't actually see the public mail, only the folders.

If you've tried this

Lincoln also sent along some advise on setting up Entourage:

One additional tip: our servers are centrally managed and I couldn't figure out who to ask for IP address or name of the WebDAV server. To get around this, I let Entourage do the automatic account setup, which filled in the name automatically. Then I did a reverse DNS lookup on that name to get the IP address number that I used as outlined above. In general, however, the automatic setup needs tweaking and I suggest a manual setup after you garner the required server information.

Your mileage may vary, but even lacking WebDAV I now have virtually everything I need.

Part 2 of Entourage 2004 support of GAL without WebDAV on Exchange Server

September 7, 2004
Michael Lincoln

I have previously reported on setting up up both an Exchange-type account and an IMAP account in Entourage 2004 in order to get the "Check Names" functionality in Entourage. Surprisingly, while the mail folders won't work in Exchange and the LDAP isn't supported in IMAP, a "dual account" (IMAP and Exchange) setup works well together.

This has allowed me to "Check Names" using the LDAP server from within an IMAP message . However, after several weeks, I have found that this solution is limited by the sparse display of GAL data inside the Entourage GUI. In Entourage 2004 "Check Names" only shows me the name and email address. In my large organization there are many duplicate names (e.g., many "John Smith's). In Windows Outlook or Outlook 2001 for Mac I rely upon the full GAL information I normally see (addresses, area codes, etc.) to mentally resolve these duplicates.

I can't see any way to get Entourage 2004's "Check Names" functionality to display the additional GAL information. Therefore, I began to look for a way to download the GAL into my contacts. However, Microsoft seems to provide no direct way to do this. My workaround is "Solution 2" and requires a Windows machine running Outlook.

1. Put the GAL entries of interest into am empty Windows Outlook Contacts folder: Procedure: click the Address Book icon in the Outlook tool bar, select your GAL or a sub-distribution list of interest, and choose File Menu-->Add to Personal Address Book. This will add all those names to the chosen Contacts folder.

2. Export the newly filled Contacts folder to a CSV-delimited file. Procedure: Choose Outlook File Menu-->Import and Export-->Export to a file--> "DOS Comma separated values", and target the "Contacts" folder you made. The export will take a very long time (almost an entire workday on my new Pentium 4 workstation!?).

3. Move the newly created CSV file to your Mac and import it into Entourage 2004. Procedure: In Entourage 2004, select File menu-->Import and Export-->etc. Entourage will bring up a widget to prompt you to "map" the various export fields to their correct, corresponding Entourage fields. You can save this mapping template for later use.

4. Voila: your GAL or a subset thereof is now in Entourage. As there is no link to your organization, you probably have to periodically repeat the procedure.

5. To sync to iCal (and onwards to your Bluetooth phone!) I suggest the excellent AppleScript "Sync Entourage-Address Book" version 2.5 followed by iSync.

Alert readers will note that you can also do a (much faster!) export using MS Outlook 2001 for Macintosh. It takes only minutes vs. hours. However, Outlook for Mac does not export _all of the fields in the GAL, but only about 90% of them. For example, it does not export the "Email Display Name" field in the GAL, only the "E-mail Address Field".

Unfortunately, my organization chooses to store the SMTP readable email address that IMAP needs (e.g.,") in "Email Display Name". The E-mail Address Field contains the (useless for SMTP/IMAP) Exchange address (e.g., "/o=MO/ou=MyOrganizationName/cn=Recipients/cn=MYORGLINCOLNM").

However, as the Mac Outlook 2001 process is lightning fast, it may be worth checking your organization's GAL structure. If you can get the SMTP address out of Mac Outlook, I'd go there first because the export is so very rapid.

Entourage over a VPN connection

August 30, 2004
Mike Armstrong

I am able to establish a session with our Nortel connectivity VPN device using Apani's Netlock v3.0 client. However, when I try to access our Exchange 5.5 server, I receive an error ( Error-3170, mail cannot be received).

When I am on campus I can attach without problem.

September 20, 2004
Clint Milligan reports having a similar problem over the same VPN device (Nortel Netlock) as previously report, only over a wireless connection:

I have a G4 Aluminum PowerBook. I am able to connect to my company's Exchange Server while connected via LAN in our office.

When I work remotely, I use the Nortel connectivity VPN device using Apani's Netlock v3.0 client. I have no problem connecting and downloading my email.

However, I cannot connect to the corporate server when I'm wireless. I use the same proxy settings for each connections type. I only change the connection type from "Built-in Ethernet" to "Airport."

September 20, 2004
Sue Frary

I have had a similar problem with VPN connectivity as posted in the last couple of weeks. I have Entourage 2004 working fine as an IMAP client over VPN to my company's Exchange server. No problems. However when I attempt to set up an Exchange account from scratch over VPN, Entourage appears to be connected and tells me it is synchronizing in the background, but it only pulls a junk mail folder and nothing else.

Waiting hours pulls no more folders. I am connected over a cable modem, so it's not the speed of the connection.

It is not the settings, as doing the same thing from behind my company's firewall results in a perfect Exchange account setup. I use IP addresses for my mail server and LDAP server, and can ping both. Oddly, the Exchange account configured within the company system will then function perfectly over VPN. VPN client is Cisco 3000. Running 10.3.5.


September 7, 2004
Bill Payne

Make sure that Mike uses the full DNS address of the Exchange server ( My problems with Exchange connectivity through our VPN centered around the fact that my host machine couldn't find the server using the shortcut names allowed within the enterprise.

Advice for Outlook 2001 with Exchange 2003 and OS X 10.3.

October 13, 2004
John Hunter of the UK describes how he uses Outlook 2001 in the Classic environment in Mac OS X to connect to Exchange Server 2003:

I have no trouble connecting to an Exchange 2003 server using Outlook 2001 with Mac OS X 10.3.5 in Classic mode. I always use a hosts file in the System Folder/Preferences. The format is:
NetBiosName CNAME DomainName

DomainName A IP_Address

Which would look something like this:


company.local A

I also put the WINS server address into Applications/Utilities/Directory Access/, and click Services -> SMB -> Configure

Finally, add the IP address and name of the Mail Server.

Entourage logon problem: keeps asking for password ("Invalid Password")

November 22, 2004
Chris Myers reports

At random times throughout the day, Entourage 2004 keeps asking me to re-enter my password for my Exchange account, sometimes doing it three or four times in a row.

I get this error message:

Mail could not be received at this time.

The server for account "Exchange Server" returned the error "Logon failure: unknown user name or bad password." Your username/password or security settings may be incorrect. Would you like to try re-entering your password?

November 23, 2004
Doug Brown

Yes, I also get this message. It doesn't happen every day, more like every 4-6 weeks.

November 23, 2004
Michael Vander Sande

I've been experiencing similar symptoms for several weeks now. Mac OS X 10.3.5, Entourage Version 11.0.0 (040405).

January 28, 2005
Peter Ennis

Like Chris Myers on November 22, 2004, I am getting this problem as well. It started right after I changed my network password using a Wintel machine. I have tried deleting the keychain, but to no avail.

Suggested fixes and workarounds

November 23, 2004
Michael White

This is because the Mac OS X Keychain is in the user keychain setting and not the login. The fix is to copy the password in the user keychain to the login keychain. 3 failed logins will disable the account with Exchange.

February 2, 2005
Marc LaPlante

If the user have selected the Save Password option in the login window, the password will get entered in the password field. The problem is that when you change your password, Entourage has no way to know the change in your main PDC. So it will still log you on with your old password and generate the Invalid Login Password error message.

The trick is to update the password field with the new password.

June 19, 2006
Laura Lunetta sent us another workaround:

I experienced this problem a few months ago, and resetting the passwords for the troubled accounts seemed to work. However, this week, I could not for the life of me resolve the password problem. When logging in, the mailbox would begin to download mail, then pop up with the "invalid password" problem.

In reading your page on this, I tried the things that I could do without involving the network administrator. The one that surprisingly worked? I logged into the account via a browser, and emptied the deleted items folder. Voila!

June 22
Matt Davies did not have success with Laura Lunetta's workaround:

I'm having exactly the same problem as described: Entourage keeps telling me that the username password pair is not right. It is though, and it's not locking me out on the Active Directory. I've tried deleting all deleted items, no luck there.

June 26, 2006
Matt Davies

I was having exactly the same problem: Entourage kept telling me that the username password pair is not right, even though it is correct. It's not locking me out on the Active Directory. I've tried deleting all deleted items, no luck there.

I've solved the problem in my instance. It was something to do with the reminders I'd put into my Calendar. After I'd removed all the repeated reminders, the ones that happened every day, the system returned to normal.

June 28, 2006
Lars Berger verified the above suggestion regarding removing calendar reminders. Other workarounds we've reported didn't work for Berger:

I use one account for Entourage 11.2.3 an 11.2.4 on several machines with Exchange. On one computer it gives me the password problem; the other Macs work without problems. I tried deleting all Entourage and Microsoft files, synced again, the annoying password dialog popped up again and again. The suggestion with the deleted mails won't work, so I tried deleting a calendar reminder and finally it works.

October 9, 2006
Ronald Bledsoe

We're running OS 10.4.7 and Entourage 11.2.5. It connects back to our Exchange 2003 servers. Two users had the login problem with mailboxes on separate servers. We found that if we set the username to be domain\username and left the domain field blank in Entourage, that the user could stay connected. No other combination of username would work. The problem started for both users at the same time. They were working on the same project.

It turns out that they were both sent an email with a ppt attachment with Japanese characters in the filename. There were also Japanese characters in the file and in the email. I don't know if that caused it, or if it was just a bad email, but I deleted the email and the problem went away. They now can use any combination of username in Entourage.

If you've tried these suggestions

Verification of Entourage "invalid password" logon fix

Wednesday, September 26, 2007
Denis Lessard verified a previously reported fix for the problem where Entourage repeatedly asks for a password with an "Invalid Password" message. Lessard said:

We're running OS 10.4.9 and Entourage 11.3.6. It connects back to our Exchange 2003 servers. The solution provided by Ronald Bledsoe settles the issue definitely: set the username to be domain\username and leave the domain field blank in Entourage. Thanks for the solution!

Another workaround for Entourage logon repeatedly asking for password

Monday, October 1, 2007
Mucai Kunyiha offered a different workaround for the the Entourage/Exchange logon problem where it continually asks for a password. In this case, the problem was Exchange server:

For four days, I had a persistent problem with Entourage and my Exchange mail service at the office showing the error below:

Mail could not be received at this time. The server for account "Exchange Server" returned the error "Logon failure: unknown user name or bad password." Your username/password or security settings may be incorrect. Would you like to try re-entering your password?

The message seemed to pop-up every 10 minutes or so. I was also not receiving or sending mail consistently, and the Exchange folder in Entourage does not show mail in my server accurately.

We tried the suggestion by Ronald Bledsoe: set the username to be domain\username and leave the domain field blank in Entourage. But with no luck.

We then re-started the Exchange Server and presto, No more error messages! Our guess is the server was clogged up with some temporary files and the delay in authentication was causing the error.

I am running Entourage 11.3.6 (070618) on Mac OS X Version 10.4.10. Our office runs Exchange 2000.

If you've tried this fix

Workaround verified for Entourage logon repeatedly asking for password

Friday, May 30, 2008

Ton Dobbe verified a suggested workaround for the Entourage/Exchange logon problem where it continually asks for a password:

The work-around by Mucai Kunyiha worked excellently on Office 2008. I experienced the same issue for over a month, day after day. Now it seems to be solved.

Side effect with fix for Entourage password problem

Tuesday, October 9, 2007

An anonymous reader said that a fix that we reported works for the Entourage "Invalid Password" problem, but has a side effect:

Attempting the solution provided by Ronald Bledsoe appeared to resolve authentication errors. However, it had the side effect of prevent shared calendar syncing from completing which hampered the display of new inbox mail receipt. I was forced to backout the authentication solution to resolve the calendar sync.

Current news at the MacWindows home page

TIP: Workaround for Entourage logon problem: keeps asking for password ("Invalid Password")

Thursday, January 31, 2008

Kenny Michelsen sent in another workaround for the Entourage 2004 problem of the password dialog continually reappearing with the error message "Logon failure: unknown user name or bad password."

Michelsen's tip:

You can usually solve this problem by entering the username with an "_" instead of "@":


Somehow Entourage can logon successfully with user@domain.xx, but forgets the logon after 10-15 minutes.

If you've tried this suggestion

One more workaround for Entourage logon problem

Tuesday, February 5, 2008

An anonymous reader reports a workaround to the Entourage invalid password problem. He use Outlook running in Parallels Desktop:

This might defeat the whole point of running Entourage, but I have found that the authentication issues can be solved by emptying trash from an Outlook client.

I generally get the Invalid Password error when I have deleted too much trash. Too much being more then Entourage appears to be able to handle, but not a number of messages or amount of data I can quantify.

When I get the error I can either clean out everything in the Entourage and MS Office cache and start from scratch, or I can log into Outlook for Exchange in Parallels and empty trash, resolving the issue.

If you've tried this if it worked for you. (For more suggestions for the problem, scroll upwards on this page.)

Current news at the MacWindows home page

Entourage synchronizing when set up not to

The problem

November 22, 2004
Kelly Johnson

I'm in OS X 10.3.6 and running Entourage 2004. In my Account Settings, under Advanced I have "Do not synchronize items to server" checked and have tried various combinations of other settings but to no avail.

Periodically throughout the day I get those annoying "Progress" windows that popup and say Updating the Inbox, or junk mail, or saved folders.

The problem is that sometimes it slows down my machine and I have to either click off the box (not "Cancel" which is grayed, the box) or wait a few seconds. Being in design/publishing where time is precious it all adds up to very annoying.

Our IT guys are 'looking into it,' but I fear as usual the well-trained computer people have no idea about anything other than Windows.

We are running an Exchange server but that's all I know at this point. Every one of the five people who are using Entourage 2004 get these little popups no matter the settings in the Account Settings tab.

We are not using POP/POP3. We are IMAP.

November 29, 2004
Tamer Rashdan

I have a PowerBook at home, I use Entourage 2004 with Exchange Server to get my work e-mail. I have the same thing happening. I can't even change any settings regarding the Exchange account. It looks like Entourage has only one setting to synchronize with Exchange that can't be changed by the user including the time interval to get new e-mail.

The Fix

November 29, 2004
Kelly Johnson, who first reported the problem, found a solution:

We figured how to get around it. Simply create a new schedule to check for new mail at any interval and the update happens within Entourage's status bar rather than having the Progress bar pop-up. Amazing that simple things like that can actually work!

November 29, 2004
Craig Edmond offers a suggestion:

I have noticed similar issues with an older version of Office, Entourage version 10.1.6. There are another set of synch options for each account under the "Tools > Schedules" menu. Double click on the schedule for the account. Next to each account listed there should be a button for "Click here for account options". You can select the folders you wish to synch and how you want to synch them, Headers Only, New Messages or All Messages. I have mine set to "Headers only" and I don't see much of a slow down.

I'm not entirely sure if this will fix the problem mentioned here but it's worth a look.

Reader Entourage 2004 public folder problem with Exchange 2000

February 7, 2005
David White

My company runs Exchange 2000. I support 140 Mac clients running Entourage 2004. We use Microsoft Exchange's Public Folders feature extensively...

In the full MAPI client Outlook 2001, Mac clients could both read and post in Public Folders and those folders were browsable. In Entourage X, Public Folders were inaccessible. In Entourage 2004 (E 2004), Public Folders can be seen.

In order to read posts in Entourage 2004, the user must subscribe to the folder as though it was a newsgroup...If normal permissions are set for the folder (posts are only editable by the owner) Exchange interprets a Mac client's attempt to read the post as an attempt to edit. An error is set in Entourage's error log that states:

Permission Error. Changes to the e-mail message "(subject of post)" could not be saved because you do not have the appropriate permission.

If permissions at the server are set so that clients can edit any post the error message does not get set. In addition to the error, the post disappears from the folder. The next post is now displayed, which prompts another error in the log. A few seconds later, the post that the client was reading reappears as unread, and the post being viewed disappears to be replaced by the next post in the folder.

And the capper to the convoluted sequence above is that Entourage 2004 clients can not post to Public Folders. There is no such function in Entourage 2004. The only mechanism allowed is to send the folder a message. Of course, the folder has to be mail enabled and maybe 20 of our hundreds of Public Folders are.

Curiously, basic Microsoft OWA through any browser does allow posting to a Public Folder. Because of the lack of support, I'm forced to continue offering Outlook 2001 as the only officially "supported" client for Exchange through Macintosh.

If you've seen this problem

Entourage in Tiger: spinning beach ball

This article has be moved to the MacWindows Tiger Reports page.

Entourage problem with proxies

September 26, 2005 -- Andy Beaven has a problem with proxy settings and Entourage:

I have a Windows Network (Server 2003) but also have a small number of Macs connected to the domain. I have no network integration issues, I can pick up roaming profiles with ease. We have an Exchange server (exchange 2003) and a Proxy server (ISA) running on the same server unit.

The Mac users use Entourage to connect to the Exchange, this works well. But in the Network prefs I have to leave the http proxy blank so that entourage will sync. The problem now occurs that those users cannot access the internet, as Safari and Explorer take the proxy setting from the Network prefs and I can’t seem to manually assign it the machine for just the browser.

Is there a way that I can get around this?


If you've seen this problem

Entourage 2004 Service Pack 2

September 23, 2005
Jason Meyer considers this version to be comparable in features to Outlook 2001 for OS 9:

The MS update that greatly improves the use of Entourage with Exchange. From my initial looks, access to Public Folders is very usable, the same can be said with using the Global Address List. The GAL still comes up blank when selected. However, it auto-finds users as you type in names, but beware it searches by display name so if your Exchange/AD admin have changed the display name to be Lastname, Firstname (like I have) you have to search by lastname. Customized Address lists are still be bit weird as it doesn't auto-find. Accessing the GAL from Calendars and inviting people is very easy, as are creating Distribution lists. With this update Entourage has almost the same basic functionality as Outlook for the PC, and its not clunky at all.

Needless to say, Entourage maybe be a better option than running Outlook2001 in classic with this update.

September 23, 2005
Pete Priel has high praise:

Wow. The Entourage update in conjunction with the server-side updates make Entourage integrate, seamlessly, with the corporate Exchange server. Prior to the update, performance was very slow. Right now I'm writing this email on Entourage running on a Mac mini while 3 other users' calendars and in boxes are synchronizing--and I can actually type! Before, even typing an email on a single user identity was frustrating.

Sharing not only is supported, now, but works great. In order to see other users calendars and contacts and email one had to create a new identity and switch between identities. This is a royal pain. Now, presuming the other users have shared an Exchange folder (inbox, calendar or contact) you can open them easily from the File menu (Open Other User's Folder...). And of course you can share your Exchange folders, easily, as well, by control clicking on them. Also, you can delegate other users to act on your behalf.

One feature that's not integrated with Exchange, yet, is Tasks. In otherwords, one cannot assign tasks and one cannot open someone else's tasks.

But wow, what a dramatic improvement.

Permissions problems with Entourage SP2 and Exchange

October 11, 2005
Jeremy Matthews

Our biggest headache is that Entourage “forgets” permissions granted on public folders (of which our accounts definitely have correct permissions). Some folks cannot delete, move, copy emails, etc. Under the previous version (without SP2), it works as it should. We've done account removal and addition from the exchange and client, both resulting in limited success. Only after repeatedly emptying the cache on certain folders to items begin to respond.

In addition, we have had to remove all previously subscribed-to public folders and re-add, so permissions would “hold”. Afterwards, we see the same problem each new day: permissions on public folders go nuts.

October 11, 2005
Michael Wilmar pointed us to an
article about the problem and reported a similar problem:

I recently installed Entourage SP2 on my Mac, which interfaces with our Exchange Servers. One of our IT people who has been helpful to me in the past contacted me shortly after I had installed it to let me know that it was available. I told him that I had already installed it. Less than 24 hours later, he got back in touch with me and asked me to stop using it until he had been able to patch the Exchange Servers to fix a bug, which he did right away.

He took the potential problem very seriously. The need to patch the servers also elicited the ritual squeals from the network supervisor about the tribulations he is subjected to as the result of my firms “acquiescing to users' demands of using non-standard equipment and unsupported operating systems.”

Whatever time was spent correcting this potential problem caused by Microsoft software engineering has been dwarfed by the time the IT department spends fixing Windows/Exchange glitches.

In any event, I don't think anyone should upgrade to Entourage SP2 without discussing this potential problem with their IT department. Apparently, it can cause serious problems with Exchange Servers.


October 11, 2005
Steven Lindsay

The Exchange Server has to be listed in the bypass field (either exclusively or exclude the local domain which the client and server belong to) in the proxy prefs pane.

If you've seen this problem

October 21, 2005
Brian J. Little describes problems with SP2, and notes that Microsoft had advised users against further SP2 upgrades just before Microsoft release the 11.2.1 update:

Everything was basically fine until our primary Exchange server went down. All Entourage SP2 users saw problems ranging from a disappearance of mail (fixed by a resynchronization) to duplication of folders (also easily fixed) to outright loss of data (fixed only by restoring from backup, a painful process). After I spent three days fixing these issues, we moved back to the repaired primary server, only to have the problems resurface, with the instances of actual data loss approximately doubled.

Two days later, MS pulled the update from AutoUpdate and issued their recommendation against further upgrades. Unfortunately, my users who already have it installed are hosed, as there is no retrograde tool (not that I would expect one, mind you).

While SP2 appears to provide some nicely improved functionality, and to repair a couple of fairly serious problems some users were experiencing, I have to say that my testing has been disastrous. Where my users were just starting to develop real confidence in Entourage, vs. the old Outlook they were accustomed to (and which, frankly, offered a lot of features still missing from Entourage), many are now actively concerned about the safety of their data. While I recognize that my situation was mostly the result of a “perfect storm” of bad timing, I have to wonder how such an apparently big bug managed to get past QC.

This incident has given our IT organization a big fat black eye that will take weeks or months to smooth over, and has made me very wary of future Microsoft product upgrades &emdash; a state of mind I had recently managed to get past.

Entourage 11.2.1 Update for fixing SP2 bugs

Microsoft issued the 11.2.1 Update to fix problems with the Service Pack 2 update, released the previous month.

November 7, 2005
Terry Brink reports that the most recent Entourage 11.2.1 update does not fix a
problem with permissions caused by Service Pack 2:

My Entourage problem sounds familiar.

Last week the auto updater for Office 2004 ran in the middle of the day upgrading to 11.2.1. When I restarted Entourage it began constantly asking me to re enter the password. Even if I check the box to remember the password it will ask again a few minutes later. I can get new mail by quitting and restarting entourage, but within a few minutes it will start asking for the password again.

Am I stuck with removing it and reinstalling and not upgrading, or is there a way to fix it?

November 7, 2005
Brad Boots found a new problem with delegating mailboxes caused by the Entourage 11.2.1 update:

Many people in our organization used the delegate option to access shared email accounts. We are a magazine publisher and these mail boxes are an important tool for filtering mail coming into the various titles. Many editors will monitor the same mailbox on the Exchange server for stories or feedback that relates to their work.

After upgrading to Entourage 11.2.1, these people can no longer delete mail in the delegate mailboxes. This is a huge problem. I have not found a workable solution.

I did open a shared mailbox as a stand alone account and set several users with the new delegated mailbox user option. This works fine for the mail that existed up until I closed the mailbox but any new mail that arrives is not available to manage.

If you've seen this problem

Entourage 11.2.1, problem with deleting email in delegate mailboxes

NOTE: A reader reports that the September 2005 patch for Exchange Server fixes this problem.

November 7, 2005 -- Brad Boots found a new problem with delegating mailboxes caused by the Entourage 11.2.1 update:

Many people in our organization used the delegate option to access shared email accounts. We are a magazine publisher and these mail boxes are an important tool for filtering mail coming into the various titles. Many editors will monitor the same mailbox on the Exchange server for stories or feedback that relates to their work.

After upgrading to Entourage 11.2.1, these people can no longer delete mail in the delegate mailboxes. This is a huge problem. I have not found a workable solution.

I did open a shared mailbox as a stand alone account and set several users with the new delegated mailbox user option. This works fine for the mail that existed up until I closed the mailbox but any new mail that arrives is not available to manage.

November 9, 2005
Jay Christianson has bit of a workaround:

We've seen this problem too. Currently, I only have one person and myself set up to use delegated mail accounts (we were the guinea pigs).

Anyway, by default, while the Exchange admins have us set for proper permissions (that work in Windows Outlook and old Mac Outlook for OS 9), we can not delete mail from these delegated accounts.

We have found, though, that if you log in to a Windows machine, and open the account from there, you can get properties of the mailbox and change yourself to owner, or whatever and then you can deleted files, etc.

BUT, we've found the effect is very temporary and flaky The other person we have testing the delegated folder has to reset the permissions from the PC fairly often because they keep reverting to not letting him in. I, on the other hand, have been able to set the permissions once from Mac Outlook, and then once my permissions reverted, I can't get them to change to allow me to delete again. Oh, this applies to individual emails in there. I've noticed that it appears I can create and delete folders from within the mailbox at will.

December 6, 2005
Steven Deutsch

I have the same issue of being unable to delete email in a delegate box. That said, sometimes I can delete email in the delegate box, sometimes I can't. And I cannot find anything consistent as to when I can and when I can't. All I know is that when I can, I try to take advantage of the window and clear out as much as I can.

February 3, 2006
Shan Younker

I’ve seen the problem also. My user is set up as the owner of the account, but cannot delete mail from Entourage. He can log into a Windows computer and delete mail. At one point he was able to delete mail then that capability mysteriously went away even though he continued to show up with ‘owner’ permissions.

May 8, 2006
Karen Zander

We have the same problem. Exchange 2003 SP1, MAC OS 10.3.x, 2004 user can not delete as delegate. Still searching for an answer to this one.

Logon failure with Entourage 2004 11.2

January 3, 2006 -- Ryan Hobus is having a problem with Entourage logging on to Exchange that he can't track down:

I have been trying to track down a solution to a problem I am having with a client's PowerBook and Entourage 2004 11.2.1 interfacing to a Exchange 2003 server. Basically what happens is that when you go to connect, it gives this:

Logon failure: unknown username or bad password -17900 no matter what you do, it won't connect. I personally have the same setup and it works just fine (PowerBook, Entourage 2004 11.2.1, and Exchange 2003).

Both myself and my client's email works great in MS Outlook 2003. Both work great with Outlook 2001 for the Mac running in classic mode. Entourage 2004 works great for me, but it doesn't work for my client.

According to Microsoft, the issue is due to Active Directory mismatching names with Entourage, but I have double checked that, and it doesn't work. I also tried about every possible combination of username, email address, prewin2k username/domain but it doesn't work. My only thought is that there is something in remote access which isn't working or blocking the access.


January 5, 2006
Alex Zaleski

I had the same problem after applying the patches to Office 2004. Once I rolled them back to the .0 release of 2004 the problem went away.

Spent many hours on the phone with MS tech and they were no help. I use entourage in a corporate environment, Tiger 10.4.3, Exchange 5.5.

January 25, 2006
Mark Cole has the problem, which he can only workaround by creating a new account:

I can reproducibly create an Entourage login failure problem by deleting a large number of files from my Deleted Items folder. After this problem occurs, the only way to get an active account is to create a whole new one.

I have had this problem since switching to Entourage from Outlook 2001 two months ago. The only way around it is to create another account, but then you lose your settings, personal data, etc. Funny thing is that the account allows you to log in once, updates everything from the Exchange server, then logs you off and wont reconnect again until Entourage is relaunched.

Very frustrating exporting all personal files from the old account, reimporting into a new account, resetting all user preferences, etc.


January 5, 2006
Michael Perbix

We have seen this and here are some things to test for.

Install Both SP2 and hotfix for Entourage available from Microsoft's Mactopia site.

Very Large inbox/sent items/deleted items. Try to par these folders down as much as possible.

If running Exchange only, turn off all send/receive schedules. I talked to MS tech support about this, and supposedly SP2 fixes the issue.

We have a number of faculty that have seen this issue, SP2 apparently does resolve it, as well as give you better GAL support and Calendars in Public Folders support. Worth the upgrade.

January 5, 2006
Tom Krebs of Melbourne, Australia, also found a way to fix the problem:

Just wanted to respond regarding the problem with Entourage problem with mismatched username or password.

When updating to Entourage 11.2 in our Organisation I had a similar problem. You have to ensure that the account field reflects the full path to the username eg.

Previously (Entourage 11.0) the account field was:

https://<path of outlook web access server>/exchange

When updating to 11.2 I had to change this to:

https://<path of outlook web access server>/exchange/<username>

This resolved the problem for me. The user should ensure that the clients PowerBook reflects this change.

Thanks to everyone else who wrote in as well.

January 25, 2006
Mihailo Despotovic offers another suggestion:

I upgraded from Office X to Office 2004 and got the same problem. The mail worked for several hours then I started getting "bad login" messages. Retyping of the password would work 10% of the time. Sometime it would work during the day but the next morning the "bad login" window would wait for me.

I tried using OWA address instead of Exchange server in the settings. Same problems. I tried all tricks -- reinstalled Office, did not apply patches after installation, applied only the SP, applied SP + the latest hot fix (which *does* update the Entourage) from the Microsoft site. I tried rebuilding the account -- this seems to help for a while but the error kept coming back. Sometimes it would work, I would restart the Entourage and then it would not. I tried deleting keys in the Keychain. I tried rebooting Microsoft Database Daemons. Nothing helped.

Finally, I solved it by switching to IMAP (which is, fortunately, also available in the company). The only caveat here is that I had to use <domainName>/<windowsName>/<emailAlias> syntax for the IMAP Account ID to make it work (this took some time do discover by trial and error).

My final conclusion is that Entourage 2004 simply does not work with Exchange (at least with the Exchange setup in my company). This is a huge disappointment since the 2004 version is a great visual and functional improvement upon the X version.

January 27, 2006
Will Moore has a fix:

This is in reference to the problem of Entourage asking for login credentials repeatedly while connected to an exchange account. We found the problem to be a corrupt binhex file attachment in the entourage users mailbox. Any time we tried to remove the file either through outlook or entourage the client software would lock up. Eventually we ended up exporting the users mailbox to a pst, purging the mailbox from the server, and recreating the mailbox. We have 3 other entourage users that have never had this problem so I don't think it is an actual entourage problem but a problem with certain message types.

Entourage SSL/Certificate problems

January 16, 2006
Kevin Ledgister reports a problem using SSL with Entourage and Exchange Server, and with Outlook Web Access:

I'm running Entourage 2004 with all the latest patches connecting to an Exchange 2003 Server. We are using SSL with a certificate created from Exchange. But our internally created certificate has a hostname mismatch so I get the error "A secure connection cannot be established because the incorrect root certificate is not installed."

I've tried manually setting up the account, using IP addresses instead of https:// and confirming the address with our IT staff.

Entourage will access our Exchange server using IMAP for email only.

The same problem also affects Safari when using Outlook Web Access: it chokes on the certificate and I get a "Cannot establish a secure connection" error. Firefox, Camino, and Internet Explorer (Windows) all note the hostname mismatch in the certificate but allow you to continue just fine to access my email.

March 23, 2006
Frederic Boldireff Vauhallan is using the most recent version 10.2.3:

I have this problem of the error message "A secure connection cannot be established because the correct root certificate is not installed" appearing in Entourage (11.2.3) when I try to connect to the Exchange server of my employer. This problem appeared with the recent upgrade of their Exchange server. They used to run Exchange Server 5.5; it is now Outlook Web Access (or Exchange Server 6.5). I have contacted the IT department, but they are not willing to help. I have tried all possible tricks, but no joy. It seems I would need to provide Keychain with a Personal Information Exchange certificate (.pfx) that my IT department will not give away.

Workarounds and suggetions

January 27, 2006
C. Royall discovered a workaround:

I'm getting the error message "A secure connection cannot be established because the incorrect root certificate is not installed" message when trying to connect to a Exchange 2003 server from the latest version of Entourage. However, I just went into the edit account menu and checked "This DAV service requires a secure connection..." under my Exchange account. After that, it connected into the Exchange server just fine. Admittedly, I still get the warning each time I start Entourage but now I just click OK and it connects to the Exchange server fine as well.

January 27, 2006
Kevin Ledgiste offered a long report with advice from Microsoft:

I was able to get some feedback from Microsoft on this issue and it is a compound one but others are experiencing this so this might be helpful.

The first issue is that the site name < exchange> needs to match the common name in the security certificate. For this example, the common name should be <>. If your OWA site name and the common name don't match, you will get a hostname mismatch error when trying to connect with Safari or Firefox. Safari won't let you in but Firefox will (I have no idea why). And Entourage just won't connect.

On Windows PC's, Microsoft has provided a way for Internet Explorer to resolve this difference by comparing the IP address of the OWA (Outlook Web Access) site and the common names. If it matches, you can click through the error window and connect successfully.

If this is the extent of the issue, creating a new certificate with the FQDN (fully qualified domain name) to match the site name only takes minutes.

Microsoft did suggest, although they couldn't confirm, that if the common name in the certificate needs to stay the same, then adding a Subject Alternate Name in the security to match the site name may eliminate the error and cause Entourage to work. You can find information how to configure that here categories/6-Security but there is no guarantee it will work.

(Some Entourage root certificate errors are not due to a hostname mismatch but from the need to properly import the security certificate. For that information, you can go to (site was down this morning) and look under the Entourage section on how solve the "root certificate not installed" issue.)

Another problem is that in some cases, a network administrator has used a domain name with an extension (such as *.dum) that can be resolved internally but cannot be resolved externally. Because of this, the common name can't use the fully qualified domain name and you get the same hostname mismatch error.

The only way to correct this is to have the FQDN changed so that it uses a proper Internet extension such as *.net or *.com. That way you can use the FQDN internally and externally and have the certificate issue correctly. Again, it may be possible to circumvent this by adding a Subject Alternate Name but I don't know if it will work.

There is good general certificate information here as well.

If you get pushback from your IT staff, you must realize that there is a security risk. If your users get used to clicking through the certificate warning dialog box (whether from Windows or Mac browsers) when accessing your OWA site, they may do the same when being illegally redirected. You want your users to be take notice of security flags. Leaving your certificates incorrect for all users is like the boy that cried "wolf".

March 24, 2006
Hemang Patel offered a workaround:

What worked for me was to make sure that in Entourage, I entered the same hostname as what is issued for the certificate. For example, if the certificate server name is, then I type the following in Entourage's server field:

March 24, 2006
Dean Shavit has a detailed article called Working around SSL Root Certificate Errors with Entourage 2004 and Microsoft Exchange. The article includes a number of screen shots.

If you've seen this problem

Events problem with Entourage 11.2.3 and Sync Services: Casablanca time zone

April 3, 2006 -- Luis Antezana warns to Exchange users avoid Entourage 11.2.3’s new Sync Services feature. It duplicated his All Day events 5 times, and a manually fixing was the only way to repair it:

After enabling Sync Services in the new Entourage update, I had this problem: my All Day events were both duplicated and changed to start at 4:00 a.m. of the previous day. Duplication continued until I had five All Day events, with two of them appearing at the wrong time, for each All Day event on my calendar. No timed events were affected. My database has been with me and behaving fine since Entourage 2001.

Somehow the time zone of each All Day event had been changed to Casablanca, Monrovia (I live in Seattle). I had to either restore from backup or manually touch each All Day event and change its Time Zone.

I noticed this time zone change after making a change in Entourage and checking iCal to see what happened and going back and forth seeing the events get weird in iCal and then Entourage. I feel like iCal may handle All Day events differently than Entourage.

As for the duplication, I have a feeling that Exchange accounts may be causing some trouble. There’s good background here and here that gives me reason believe that Entourage with Sync Services enabled may be doing a Bad Thing if it’s being used on more than one Mac and each has an Exchange account in Entourage and both .Mac and iCal synchronization enabled. Your data should be syncing to only one source, but in this scenario Entourage is syncing to two: Truth (this is the master database for all info handled by Sync Services) and Exchange, and it looks like there’s some room for error here.

An example flow would be as follows, given a Mac at work and one at home, with Sync Services, iCal, and .Mac enabled on both as under the scenario just mentioned:

  1. Change in calendar item in Entourage at work.
  2. Change goes from Entourage at work to Exchange Server 2003 at work and to Truth at work.
  3. Change goes from Exchange Server 2003 at work to Entourage at home AND change goes from Truth at work to .Mac online to Truth at home.
  4. Entourage at home wants to update Truth at home with the data it got from Exchange, while Truth at home wants to sync its new data to Entourage at home. Maybe they each update each other, and this is the source of the duplication.

Once I disabled the Sync Services in Entourage I had no more additional duplication, the All Day events I manually changed back stayed correct, and the duplicate All Day events that I manually deleted stayed deleted.

I would recommend at this point that Exchange users not enable Sync Services, or at least proceed with caution, if they use iCal and .Mac and Entourage with an Exchange account on more than one computer.

If you’ve seen this problem

Play it again, Sam: Entourage/Exchange events reset to Casablanca time zone

Monday, October 1, 2007

Ben Morris in Australia has a problem first reported last year with Entourage where all-day events get changed to "Casablanca, Monrovia:"

I am writing about the weird problem with the Entourage/Exchange/iCal/.Mac and all-day events combo where the event gets stretched and the time zone gets changed to Casablanca, Monrovia.

I note that another user has had this problem, but I am unable to find a resolution on the web, apart from changing all day events to timed events.

Another odd thing is that Casablanca is in Morocco. Monrovia is in Liberia, well over 1000 miles away. Both are in Greenwich Mean Time.

If you've seen this problem

Entourage/Exchange "Casablanca" time zone problem can block events

Wednesday, October 3, 2007
J.B. Zimmerman also has the Entourage problem where the time zone for events get changed to "Casablanca, Monrovia." He described the problem this causes:

Oy gevalt, do I have it. All Entourage users in our firm have their time zone set to Monrovia; I *think* it has to do with the fact that the Exchange server uses GMT for its time zone and Entourage doesn't know how to handle that other than finding a Mac time zone that is GMT. The problem comes when that time zone is then applied to events, and the delta is *re*applied at some point in the process.

In my case, I will see events "blocked" at the proper time for my time zone, but whenever I *view* the event (or get the alerts) it lists it using 'local' Monrovia (GMT) time. So basically I have to do mental gymnastics whenever I get a meeting request or change alert.

If I go into my calendar view, they all show up at the proper (local) time, i.e., with the offset from GMT applied.

It drives me crazy. We're on Exchange 2003, with all current service packs.

If you've seen this problem

More on Casablanca time zones with Entourage

Friday, October 5, 2007

We have more reports of the Entourage problem where time zones for events get changed to "Casablanca, Monrovia," which is Greenwich Mean Time (GMT).

J.B. Zimmerman clarifies his previous (above) report :

Just FYI, in my case it is *all* events, not just all-day ones.

Justin Rogers reports:

I also have this problem. It's a PITA. All-day events created in iCal get put into Entourage as all day events in Casablanca, Monrovia, but they look like it's on one day in my calendar. In Outlook/Exchange/Blackberry, they span two days, and it's very annoying to have that on my Mobile and everywhere else. I'm in the same time zone as the server, and everything is set for GMT. Not sure what a fix is, other than to go into entourage and create everything, or once created in iCal, go to entourage and change to EST.

Another take on the Entourage Casablanca problem

Wednesday, January 9, 2008

Bruce McIntosh is seeing the previously reported problem with Entourage/Exchange reverting to the Casablanca/Monrovia time zone:

I, too, have experienced this problem. I am trying to sync a PC at work with Macs at home and a Treo. The Treo syncs OTA via Exchange (most of the time). The Macs at home sync with each other via .Mac. Outlook communicates with Entourage via Exchange. Entourage syncs (using sync services) with iCal, which syncs with .Mac, which syncs the Macs at home.

All this works, except somewhere along the line Outlook entries change to GMT-0, Monrovia/Casablanca. There is no way to stop it and editing the entries doesn't help as they simply revert back to Monrovia.

Is there some way to turn-off time zones in Outlook, or Entourage, or Exchange? Time zones can be turned off on the Treo and in iCal, but that does not seem to affect anything.

I've tried using Snerdware's Groupcal, which seems to work but causes a proliferation of calendars and duplicated entries, so after a week of use is not terribly satisfying; nor does it seems very reliable. Still searching for the holy grail of reliable data syncing.

If you can shed some light

Entourage Casablanca time zone issue seen with Entouage 2008

Wednesday, February 20, 2008

Mark Greenberg is having the Entourage problem where all day events change from EST to Casablanca time zone. We've had many reports of this before, but his is the first we had with Entourage 2008:

I'm having the problem in spades! I upgraded to MS Office for Mac 2008 and have an Exchange server at work. Entourage and iCal run on multiple computers, though only my work computer is set to sync between Entourage and iCal. I have corrected my all-day events back to EST and see that they are switched to Casablanca just about every time I launch Entourage.

It appears much worse with Entourage 2008. All my computers are now running it.

Also, a new problem has occurred since I loaded Office 2008. My calendar items in Entourage disappear and reload nearly every time I launch Entourage. There is no loss of data, but it slows things down considerably.

If you seen these issues with Entourage 2008

More problems with Entourage 2008 syncing, Casablanca time zones, dup events

Thursday, February 28, 2008

Kurt Waltenbaugh responded to last week's report of readers unhappy with Entourage 2008's abilities to sync with handheld devices. He is also seeing the Casablanca time zone problem reported with Entourage 2004:

Yes, I just moved to Leopard and Entourage 2008. I had been syncing to a Treo 650 with Missing Sync for about 18 months successfully. With the upgrade, everything has gone to hell: duplicate events all over the place, events set to "Casablanca, Monrovia" time zone.

A smaller version of this happened when I started with Mac/Missing Sync last year, but was resolved relatively quickly. Now, no one seems to know how to resolve the issue.

Note : my colleagues with iPhones have none of these problems. Time to switch?

More on Entourage 2008 and the Casablanca calendar shifts

Monday, March 3, 2008

Yaron Elad is seeing the problems with Entourage 2008 calendar events and the "Casablanca" time zone problem:

Me too! I thought I was going crazy. I have an iMac running Leopard 10.5.2 with iCal synced to Entourage 2008 which is connect to my Exchange Server at work. I am seeing the same behavior described by others. Any all-day events created in iCal wind up shifting to 24 hour long events spanning 5 PM to 5 PM from the day before to the day of the actual events. The time zone on Entourage says Casablanca, Monrovia. I have the time zones in iCal and Entourage set to Pacific Time where I am. The event looks OK on iCal.

The problem started with Entourage 11.2.3 about two years ago, and is now being reported in Entourage 2008.

If you have a suggstion

TIP: Workaround for Entourage events "Casablanca" bug

Wednesday, April 28, 2010

Kim Collier found a workaround for the old problem of Entourage/Exchange problem where all-day events get changed to "Casablanca, Monrovia:"

I found a fix.

  1. Open an event in Entourage
  2. Click on "Event" on the top bar
  3. Scroll down to "Time Zone"
  4. Select your time zone

That's it. You only need to do this for one event and it sets the Time Zone for all events. This has completely cleared up my problem with the changes that happen in Outlook after syncing with Entourage through Microsoft Exchange.

If you've tried this suggestion

Read current news on the MacWindows home page.

Can’t see updates to recurring calendar events on Exchange: Exchange Vista update blamed

This is one of at least two problems with Entourage caused by the KB 911829 update for Exchange Server. (A second bug is reported below.)

Version two of this page may fix the problem (see below).

May 22, 2006 -- Susan Frierson reports an Entourage problem with updates to recurring events:

We are having this problem: the update email comes through, but it is blank. I believe it is related to Exchange Server.

We are using Entourage 2004 and 10.4.6. If I remember correctly, the update feature worked a couple of months ago. Mac OS X may have been updated since then, so possibly the issue lies in this particular version.

May 25, 2006
Mario de Greef says that this problem is caused by an Exchange Server update that Microsoft issued to support Windows Vista beta. The Microsoft update is called "Update for Exchange 2003 (KB 911829)."

We also had the empty mails, calendar's etc. after installing MS KB911829 on our 2003 servers. The solution was removing the MS KB911829 until Microsoft Releases a patch.

Microsoft describes the update:

This update restores functionality to Microsoft Exchange Outlook Web Access due to changes being made to Internet Explorer in the upcoming Microsoft Windows Vista Beta release.

If you've seen this problem

More Entourage problems caused by Exchange KB 911829 update: blank email replies

The article directly above reports that Exchange Server Update KB 911829 causes a problem with Entourage where users can’t see updates to recurring calendar events. Here, a reader reports that this isn’t the only problem caused by the update, which Microsoft released to support the Windows Vista beta:

May 31, 2006
Tom Francais

When an OWA user replies to an HTML email, the reply may appear blank to an Entourage user. Our Entourage users reported receiving blank email messages just hours after MS KB 911829 was applied to our Exchange server. We're still waiting for a fix from Microsoft.

Steps to reproduce the problem: 1) Send a new HTML email from Outlook 2003. 2) Reply to email from OWA using IE in Windows (the OWA Premium interface) 3) Open the reply in Entourage. Body of message appears as a horizontal line without text.

It appears the editor in OWA's Premium interface (available only through Internet Explorer in Windows) is generating bad HTML. Entourage doesn't know how to handle the bad code. The same HTML message is displayed correctly in other email clients (Apple Mail, Thunderbird, OWA, Outlook). If a reply is sent from OWA using Firefox or Safari (the OWA Basic interface), HTML is converted to plain text and is readable when opened in Entourage.

Here are a few links that I found helpful:

June 5, 2006
Craig Chambers

We are having this problem as well and I can confirm that it happens after installing the KB 911829 patch. After we installed the patch, all our Entourage users reported getting blank emails. So far we haven’t found a fix and I am considering trying to uninstall the Exchange patch since we have no versions of the Vista beta in our office.

Version 2 of Exchange KB 911829 update may fix the Entourage problems

June 5, 2006 -- Last week, Microsoft has issued Version 2 of the KB 911829 patch for Exchange Server. The first version of the KB 911829 patch caused a problem with Entourage where users can’t see updates to recurring calendar events. It also causes a problem where Entourage users receive blank email messages.

James Caudill describes the "patch of the patch:"

You will notice that the download has been updated with a 'V2" in the binary name (Exchange2003-KB911829-v2-x86-ENU.exe). This was released on may 31.

Erik Bowling also tried it:

I just got word of the fix for issues with 911829.  I had to uninstall the patch to keep my 30 Mac users happy. Not a lot of fun!  Here is what Microsoft just sent me:

Dear Valued customer the release of the hotfix update to KB: 911829, is now available for download on the web… Mode of release: The Version 2 of KB 911829 can be downloaded from the download center…

Entourage email attachments fail to get thru Exchange

June 9, 2006
Rich Ailes can't send Entourage messages with attachments. He gets a –3259 error instead. His report:

Our company now has its own Exchange 2003 system and the admins have tweaked settings to allow the Entourage Exchange client to work well. My particular site uses Public Folders extensively and the Entourage Exchange client allows us to see these and use them, something that was missing in the IMAP client.

Then I tried sending emails with attachments and to my dismay anything over a few hundred K would just hang for a few minutes and eventually fail, returning an error -3259 with the message "An operation on the server timed out. The server may be down, overloaded, or there may be too much net traffic", which is an obvious erroneous message because the server and client continue to sync up, displaying the same messages in my Inbox that I see on my PC Outlook side (I work on both platforms).

This is a real showstopper as our company is heavily graphics oriented with lots of PDFs traveling around via email.

June 14, 2006
Terry White wrote:

I have seen this problem with sending attachments over 300KB. It will hang right around 300KB during the sending process. If I stop it, disconnect from VPN, reconnect to VPN and wait for all my connections to start syncing up again (calendars and such) and then send, it will usually go through.

June 14, 2006
Ron Vyskocil:

We are having the same problem with Entourage and our Xserve. We recently installed a new Mac Mini Intel Core computer as our email station and loaded the latest Entourage and it's update. When we attached to the XServe over our network and try to attach a file for sending with the emails, Entourage locks up and does not continue making a force quit the only way out. If we copy the attachments to the Mac Mini desktop from the server first, then attach file, it sends fine.

June 14, 2006
Stephen Gageby is not seeing the problem:

Our company is using a 2003 Exchange Server and I'm running a G-5 Mac dual processor, with Mac OS X 10.4.6, and Entourage as my E-Mail application. I’ve had no problems moving files, mostly JPEG pictures, through our exchange and the Internet.  I do reduce each file to somewhere around 500k or 600K in size, but our folks send a lot of big graphic files and we are having no problems.

A suggested fix

June 16, 2006
Rich Ailes first reported the problem of Entourage email attachments failing to get through Exchange. Now he offers a solution:

Last week I reported an Entourage Exchange client failure sending large attachments. We are using version 11.2.3. I'm happy to report that the failure is now fixed, although the fix is a bit incomprehensible.

I had set up the Exchange client while we were still connected to our old corporate sponsor's Internet gateway. So our Exchange Server was on our new corporate network while our Internet access was using the old corporate proxy. (This is a WAN network connected thru VPN devices and we were transitioning away from a former corporate host).

This week we completed the final part of a network migration, switching Internet access to our new corporate proxy. When I went back to test the attachment issue again, the attachments went through fine.

So somehow having our corporate Exchange server and our corporate proxy all on the same network segment did the trick.

TIP: Problem and fix with attached Office files

June 26, 2006 -- Steve Neale found that the 11.2.4 Update to Entourage 2004 fixed a problem he was having with attached office files on an Intel Mac:

About two weeks ago I logged a comment at Mac Mend about Entourage's failure to download attachments, particularly PowerPoint (but often Word and Excel files too) onto my MacBook Pro. The response that I got was that this was a common problem and that no one seemed to have any answers.

I was about to switch back to Mac Mail and Safari, when I noticed the 11.2.4 update at Mactopia. I'm happy to report that Entourage now seems totally compatible and that I have had no such problems since.

If you've seen this

Problem with changing Entourage/Exchange shared calendars

July 10, 2007
Paul Ukena is having a problem with Entourage making changes to shared calendars on Exchange Server:

The latest patch to Exchange failed to fix a problem for us. We have secretaries sharing their bosses' calendars, with owner permissions, and they can't add or delete anything to the calendars (they can add stuff, it just doesn't synchronize with the server).

July 12, 2006
Tom Francais

In reference to Paul Ukena's problem posted July 10, 2006: I have the same problem. Entourage users can't make changes to a shared user calendar. No errors appear; the changes just never sync to Exchange. Changes made to the to server by some other method will sync to Entourage. The Entourage user has Owner permission to the shared user calendar. I do not see this problem with Public Folder calendars.

Entourage users are a small, but growing, group here so I don't how long this problem has existed. I first heard of it about a week after we applied the latest patch to Exchange.


July 17, 2006

I have seen this same problem when one of the shared users is running a PC. I have wasted much time on this issue...

In my experience I have had limited success by forcing the Entourage client to update itself. But this is very limited. Other workarounds was to send a meeting or event to the intended victim. Overall I've been very unhappy with this since the impression to other users is that it's my fault.

July 20, 2006
Bill Bryson

Ever since we applied the last security patch to Exchange in late June, Entourage users who had been granted "Editor" (write) permission to other shared Exchange calendars no longer are able to update events on the shared Exchange calendar properly (unable to sync).

I have since determined the following:

1) Entourage users currently can NOT place calendar events marked as "busy" on a shared calendar if the event is in the current month (July) or the following two months (August and September).

2) Events marked as "busy" CAN be synced to the shared Exchange calendar if the events being added/updated are in the past (before July) or more than two months in the future (October or beyond).

3) If an event is marked "free" using the Options toolbar button when adding the event, it can be added to the shared Exchange calendar regardless of its date.

It appears there is an access permission problem related to the update of the free/busy database used by Exchange with the latest Exchange security update in place.  We have a clustered front/backend Exchange environment. We were not able to replicate the problem in our test Exchange environment which is non-clustered front/back end.

Workaround: We have determined Entourage users can access a shared Exchange calendar if delegation is used to grant access rather than just sharing permission setting.

August 1, 2006
Thomas Francais

In reference to Bill Bryson's workaround posted July 20, 2006: I can confirm his workaround allows Entourage to save changes to another user's calendar.

August 3, 2006
Paul Ukena

Many thanks to Bill Bryson for his fix. Changing the status to Free worked for us, and I now have several very happy secretaries, who don't mind the extra step involved since it fixes the problem.

If you've tried this workaround

MSN Messenger problem with Entourage logon

July 20, 2006
Adrienne Webb reports that MSN Messenger causes a problem with Entourage logging on to Exchange:

After installing MSN Messenger, the customer connects to Exchange Server, appears to sync email. After a few minutes, error message says error-logon failure-bad user ID or password-do you wish to retry? If you ignore the message, you can see in the background files indicate they are being updated (but they aren't).

When all the MSN Messenger files and preferences, and the office notification preferences, are removed, and the Entourage database rebuilt, all is OK. The files I removed are listed below (I am sure they all don't need to be removed, but one of them is the culprit):

Mac G5 with 10.4.7/Entourage 11.2.4/Windows Exchange server MSN Messenger (current download from Mactopia).

This doesn't appear to be related to the Entourage logon problem described above.

If you've seen this problem

Outlook characters don’t translate to Entourage

August 28, 2006 -- Paul Ukena's Entourage clients aren't getting all of the text characters from the Outlook Windows clients:

I have a client who uses Entourage with an Exchange server. When clients send him email from PCs (I assume from Outlook), they often use characters he can't recognize. The most egregious example is fractions: "1/2" on the PC translates to "≤" on the Mac, for example.

I can't find any information on this specific problem. If I could at least find a table of which characters on the PC become which characters on the Mac, I could at least make my client a Decoder Ring.

August 29, 2006
Jason Westlake:

I have seen this problem on several of my Mac users here at our office.  The fraction problem is the most frequent, and they usually appear as the "pi" character.  We're running Mac OS X 10.4.7 and Entourage 11.2.5.

August 29, 2006
Brad Allen notes that he does not see the problem:

We could not duplicate this problem when sending from Outlook to Entourage using the following formats: HTML, Rich Text, and plain text. We are using current versions of both clients with an Exchange server (which I assume is also current, since we are just at the beginning of migrating from Lotus Notes/Domino to Exchange).

A Fix

August 29, 2006
Geordie Korper, Group Logic’s ExtremeZ-IP Support Lead, sent us a fix:

Windows uses a slightly modified version of the standard Western European (ISO/IEC 8859-1) character set. The Windows version is properly called Windows-1252. The problem is that Outlook labels the text "Content-Type: text/html;charset="iso-8859-1" even though it is using Windows-1252 and then Entourage tries to interpret it as such. However, Entourage will properly interpret the characters if you choose "Western European (Windows)" from the Format->Character Set menu.

August 29, 2006
Markian Hlynka agreed that text encoding is the source of the problem:

This sounds like an encoding problem. Windows is really good at lying about text encodings. If you set the encodings to utf-8/ unicode, the problem should go away PROVIDED Windows respects the setting. Of course, the original keystrokes may no longer work; they may have changed!

August 29, 2006
Michel Paris of Montreal, Canada found that upgrading to Tiger 10.4.6 fixed it:

I've had the same problem for years with emails showing "fraction-like" characters from PC from outside our company (Oddly enough, those coming from PC inside the company were showing up just fine). Even weirder was that doing a reply would cause the message to be displayed correctly in the reply window.

The issue was with 10.2.x and 10.3.x. Upgrading to 10.4.6 solved the problem.

If you’ve seen this issue

Reader reports Entourage invitation buttons grayed out

December 28, 2006 -- Andres Torres reports a problem with Entourage that prevents the user from accepting invitations. The problems started when he tried to switch to Apple Mail:

We run a network with Windows 2003 Server and Microsoft Exchange Server. One of our users is on a Mac and uses Entourage as his mail editor. Everything was fine until he tried to change to Apple Mail instead of Entourage. As the change did not work, he came back to Entourage and since then when he is sent an invitation from any other user, regardless of the invitation coming from a PC or Mac he cannot accept it.

If you go to webmail and check his account through webmail you he can see and accept invitations but if he tries to get them through Entourage it did not work. We thought the problem was his profile on the machine so we configure another machine for him and the problem still happening.

If you’ve used the seen this problem

Entourage/Exchange invitation button grayed out

Thursday, December 4, 2008

Mic Stremel reports seeing a problem Entourage and Exchange where the invitation is grayed out and not available. We first reported the problem two years ago. Stremel's report:

I say your report on this problem, and have run into a couple of issues involving this situation. I have seen two users running Entourage 2008 on an Exchange 2003 environment. In some cases they can accept or decline meeting invites, but other invitations the buttons are greyed out. There does not appear to be any consistency on when the buttons work or not. However, I had not set up these users on Mac Mail. And, they can use Outlook Web Access, and/or Outlook on a Windows machine to accept/decline meeting invites, but NOT through Entourage. I've uninstalled/re-installed Office, and also created a new Identity for Office. Still, no luck.

I've searched far and wide on most Mac/Entourage blog sites, and no clear answers.

If you've seen this problem

Reader can't accept invitations in Entourage

Wednesday, September 29, 2010

David Kline has a problem with Entourage that prevents the him from accepting invitations:

My issue is very much what Mic Stremel reports on this page. Oddly enough, Mic works just up the hall from me. I'm not the user he reports consulting with but another am another user in his company.

If you've seen this problem

Entourage not showing attendee status

March 14, 2007

After having Exchange Server upgraded, Miriam Werquin is having a problem with Entourage 2004 not showing attendee status:

IT recently upgraded to Exchange Server 2000 SP3 rollup (not sure if April or August version). I have a PowerPC G5 Mac, 10.4.8 Build 8L127.

I can send/receive email, make and accept appointments and see schedules, yet the "view attendee status" always shows "no response." I know that they receive the appointments because it logs on my calendar, the OWL calendar, and I get an email message saying they have either accepted, tentatively accepted or declined.

Any ideas on how to resolve the "view attendee status" issue, other than manually updating the popup?

March 16, 2007
Peggy Commodore verified the issue: "We are seeing the problem described. Any solutions?"

March 16, 2007
Michael Wilmar offered one solution:

I have had the same problem. No idea what causes it. But now seems to be working. The only thing I've done recently has been to install the Office updates, including most recently the Daylight Savings Time update. So maybe MS fixed it somewhere along the way and just didn't tell anyone. Maybe whoever is having this problem should make sure that he or she has installed all updates and then see if it works.

March 16, 2007
Chuck Cribbs also has the problem:

We are moving to a hosted Exchange Server. I have no idea what version of Exchange they ( are running. They are a very large outfit so I would assume they are at Exchange 2003. We are an all-Mac shop, about 60 Macs, and we are seeing the very same thing. However, before we switched to Exchange, attendee status worked fine (we were hosted using POP3).

You can set the status manually if you are the one who created the meeting. But it is not automatically updating at all in Exchange.

March 16, 2007
Tom Chiara:

I have the same problem that Meriam Werquin is having. I used to be able to see the Attendee Status, but now I can't - no response. I work for a very large company on a huge network (one of the world's biggest companies) and I'm part of a renegade group of Mac users, so we can't complain to IT. I have no idea what version of Exchange IT is using, but I'm using v11.3.3.3 of Entourage 2004 on a G4 PowerBook, on 10.4.8. Again, it was working, then it stopped showing attendee status, but that's been maybe a year ago, or so (estimate).


April 2, 2007
Andrew Plant has a suggestion for the issue of Entourage not showing Attendee status:

I found that I had to use the fully qualified domain name/public, then the attendee status showed up again. Before, it was just grayed out.

April 30, 2007
Andrew Rouner had a similar solution:

I had same problem. The free/busy server usually has "fully qualified servername/public." All I did was to add an additional slash at the end of this address after "public" and at least in one instance, this seems to have fixed it. Only time will tell if this actually did completely fix the issue.

In this case, I used the same name for the free/busy server (in the Public Folders Server field of the Advanced tab of the Accounts drop down menu under Tools) as for the Exchange Server itself (also in accounts, in the first tab, account settings, in the "Exchange Server" field).

UPDATE: On May 2, Rouner told us that he discovered that the "fix" didn't stick:

On second thought, I'm not sure what happened with the one event (where it DID seem to work) but I haven't been able to duplicate it, and from what I've seen on other postings, it's an issue that can only be corrected by changes on the Exchange server (not on the Entourage client). Sorry for the red herring.

Entourage/Exchange login failures

There are a number of suggestions below, but the most relevant involves non-roman charactors in email. Below that is a description of a Microsoft hotfix that solves the problem. Another fix is here.

March 26, 2007
Edward Earle reports a problem with Entourage clients starting to be unable to retrieve email, and has a workaround:

I would like to report a growing problem with our Entourage and Exchange network at the International Center of Photography in New York. We have 20 Entourage clients and 60 MS Outlook clients.

We run Exchange 2003 on Windows 2003 R2. Starting about two months ago, occasionally Entourage clients have not been able to retrieve mail. Entourage will start to prompt for password and rejects it, and states:

"The server account returned the error "Login failure: unknown user name or bad password"

After a few attempts, you cancel and it goes off line. At this point some recent mail will appear. While it states that it is off line, it will (periodically, continue) to send mail after the username and password are re-entered. If one uses OWA to then connect to the server, if you delete mail via OWA, the deleted items folder in Entourage is refreshed, while again, no new mail appears.

The way we repaired it was to create a new mail account on Exchange and import all the mail into it, then delete the database on Entourage and let it sync up to the new mail account.

However, I do not think that it is a problem with Entourage itself but with some strange permissions issue between the Mac client and the Exchange account itself. This became very clear when my own Entourage client at home AND the one at work started this behavior at the same time. One client (at work) is on the LAN, the other is using http to connect. Both failed to properly connect and will not retrieve mail (while outbound and updates of deleted items and junk mail continue unabated.

It is quite strange the way it just hits one account at a time.

Entourage 11.3.4 (while this problem showed up on much earlier versions of 11). Mac OS 10.4.8 (and again, this happened with earlier versions of Tiger).

Exchange 2003 v. 6.5.7638.1 (native mode, no pre Exchange 2000)

More workarounds for Entourage/Exchange login failures

April 2, 2007

Many readers are reporting the problem of Entourage clients unable to retrieve email, with a "login failure" error message. Readers are also reporting different workarounds, including turning off AirPort, deleting email, deleting accounts, emptying the junk mail folder, and others.

Edward Earle who first reported the problem, says his workaround no longer works:

Our "work around" did not work this time. We created a new account on Exchange, imported the brick-level data, and the Entourage client still failed. Other Entourage clients continue to work just fine. Strange behavior. We are going to try https: as a more secure method. My feeling is the an MS update in January or February for Win2003 must be a culprit.

Ed Coye blames the 11.3.3 update:

We have seen this issue as well. It seems to clear itself up after an hour or so. However, the problem can be made worse if the user continues to try and login and Exchange Server is set to lock out their account after so many tries. If you are trying to troubleshoot this, make sure to have your administrator check to see if you are locked out first.

We have not found a solution but have noticed that the problem is getting worse after upgrades to 11.3.3.

Chuck Cribbs turned off AirPort:

We have 60 Macs connected to a hosted 2003 Exchange Server in Denver ( We just migrated to this past weekend. I am starting to see some of what was discussed by Mr. Earle.

However, once I had our Mac laptop users turn off Airport wireless access (I thought maybe it was a networking issue) the problem seemed to go away. I only had 2-3 users, all with laptops, who had this issue. None since Airport was turned off.

Eric Rutherford deletes email messages:

I am currently experiencing this issue with at least 2 users. A list of troubleshooting steps I have taken.

  1. Reinstalled Office 2004
  2. Renamed the old database and had it create a new one
  3. Tested on a new computer
  4. Updated Office 2004 to the latest

Based on these troubleshooting steps I think I can comfortably say that the issue is between Entourage and Exchange. I have done some research online and I have found some people were able to resolve this issue by removing emails that came in around the date that the issue started. Since these are not my inboxes I don't have a good date to go by and I would be deleting random emails, (not a good step in my opinion).

An anonymous reader said that deleting email causes the problem:

I have been experiencing this problem at work for many months. The problem appears directly related to multiple deletes or moves of messages from the inbox during a single session. Our only solution is to delete the Entourage account on the client, along will all associated Microsoft preferences and database files, and then reset up the account.

Bill Vader empties the junk e-mail folder:

We run Exchange 2003 on Windows Server 2003 SP2 (not R2). Out of about 100 Entourage clients (including myself) I have 2 that occasionally get the "Login failure: unknown user name or bad password" error. I've found that when I empty the Junk E-Mail folder, the account seems to sync again. I've instructed the two clients to empty their junk mail folders when this happens and they haven't complained since. My 2 cents,

Brian Benton finds the problem to be random:

We have had this issues for several months. I typically see this with a user connecting over our VPN to our Exchange 2003 server. 1) This does not happen to all users 2) this does not always occur with the same users 3) changing the account settings -- specifying IP or webgateway seems to kind of fix it temporarily. 4) Some users never have this problem 5) one user inside the network has this problem (just started late last week) 6) sometimes this problem just fixes itself...

This error is very odd and inconsistent. I assume the work around they did an "empty cache" to resync data after the Exchange account was moved and recreated.

The only consistent issue I have seen, which started this past Friday, was from an internal client (not connecting over the VPN). This account simply no longer works from Entourage.

April 4, 2007
Brian Benton adds to his previous post about problem of Entourage clients unable to retrieve email, with a "login failure" error message.

I can setup the account that has problems and will have no problems setting up, authenticating and verify the user and his (or her) account. The account may even appear to work for the first five minutes, so there is definitely something different with how Entourage connects during setup vs. actual use.

I first noticed this problem with VPN users (not sure if I mentioned this before). We have two VPN setups - one where users connect to our VPN URL (via their own router) and other setup where we provide a configured router that automatically and always connects to our VPN (these have different subnets as well). Users connecting to the main VPN (regular router) can have this authentication issue, however it is not consistent - sometimes it goes away with no server side action. I have not seen this issue with users on the configured router (they are CISCO I think, though it shouldn't matter). We only have two Mac users using the CISCO routers (configured to connect 24/7/automatically to our network).

April 11, 2007
Ron Gonzalez tried the suggestions described on our Entourage Reports page, to no avail:

I thought the problem was isolated to one client, but it's happened to a second in our organization. Both users have the same first name, strangely. I've tried turning off the AirPort, recreating accounts, changing passwords, removing mail from all mailboxes, deleting the local MSOffice database, reinstalling MSOffice 2004, and routing through OWA, but nothing resolves the issue. The web client still functions normally with both accounts, but it's limited in functionality, as you know. Both clients are fairly high up in the chain of command around here, and it doesn't look good for me if this can't be resolved. One client has given up entirely and is using Gmail as their primary mail program. I've even considered an early adoption of Exchange 2007 as a possible solution.

April 11, 2007
Sheraz Daya has also tried a number of things without fixing the problem:

I have been experiencing this problem for a couple of months (mid Jan or so onwards) and have tried all sorts of solutions including, moving all items out of the inbox, deleting junk, creating a new account, new databases clean installation etc. etc. Just when I think the problem has been sorted, it happens all over again.

I look forward to hearing of any further ideas about fixes. At this stage I am so exasperated, I am considering dumping Entourage altogether. Are there any other integrated software alternatives for Macs?

Note: One alternative to Exchange is Kerio MailServer, which works with Macs and Windows PCs. For Macs only (without Exchange Server), there's Now Up-to-Date.

April 16, 2007
Craig Doran said that using the Microsoft Database Utility that comes with Office solved the problem:

Ultimately, verifying the database using the Database Utility showed that there were some problems and using the utility to repair them fixed this problem.

April 16, 2007
Lewis Riley, however, reported that this and the other suggestions we've reported didn't work for him:

Out of 15 Mac clients, I only have one experiencing this issue (G5 1.8 GHz running 10.4.8 with all Office updates). I have followed a few of the easier suggestions (repairing database, recreating Entourage account, deleting junk) to no avail. I also tried recreating the keychain, but that did not help either. The user reports that restarting the machine will allow them to connect to their email account again. I suppose the next step is to try reinstalling the application, and then the OS. Lovely.

If you've seen this problem

Non-roman spam may be at root of Entourage login problem

April 23, 2007
Sascha Segan of PC Magazine told us that non-roman characters in emails, such as Chinese spam, cause the Entourage login failures that we've been reporting. Segan wrote about it in his blog and sent us this note:

I ran into the Entourage login problem at PC Magazine Labs recently. I talked to a senior tech support person at Microsoft and they gave an interesting explanation.

At least, that's what they SAY is causing the problem.

In his blog, he offers a fix:

The solution is to delete all of those non-Roman messages, and then use Outlook Web Access via Safari -- not Entourage -- to purge your Deleted Items folder.

April 26, 2007
Jeremy Matthews confirms this explanation and fix:

We've seen this before, and its definitely caused more than a few problems within Entourage.

The fix is on-par with our solution: delete non-roman spam. Unfortunately, this usually means going through pages and pages of spam and deleted items and sometimes an inbox or two in webmail (Outlook Web Access).

Best thing you can do is to find out the exact date they began having difficulties/errors, and purge non-critical emails (in any folder) during/after that date.

We've seen a variety of problems stemming from this. A real pain.

Sheraz Daya has a somewhat different workaround, but related to email:

Since my last communication I have discovered that removal of all email from the Inbox and transferring these to a main folder (not a subfolder of the InBox) seems to rectify the problem for a while. When the problem recurs, I again transfer all messages out. This suggests that there really it is a received email message in the Inbox that causes the problem.

May 7, 2007
Edward Earle, who first reported the problem Entourage clients unable to retrieve email, with a "login failure" error message, sent us a follow-up note. He said that the suggestion from Sasha Segan of PC Magazine did the trick:

I just wanted to thank you for the range of responses that came in since my note of March 26. While we has some success with the laborious export, new account creation, and import, the final key was Sascha Segan's note about non-roman characters. We purged several accounts of Asian email messages, killed the cache and sure enough, the mail account came back up. As soon as a new non-roman message came in, the mail stopped syncing. Once that was removed, and Entourage was restarted, the program worked well without the need to remove the cache a second time.

I am now searching for a way to block all non-roman email (or simply change Entourage's formatting to ASCII). Apple mail has worked well with Exchange server as an alternative but missing that critical calendar application that is so central to Exchange.

May 7, 2007
Eddie Storey said the problem doesn’t happen with Outlook Web Access:

I have the password problem too. It works flawlessly from home using Outlook Web Access over cable modem. Using Entourage, either CAT5 or Wireless, I get the repeated prompt for password only when I'm on local network or on VPN to the same network as the Exchange Server.

MacBook OS X 10.4.9 and Entourage 11.3.3 on Windows 2003 Server with Exchange 2003.

Another take on Entourage/Exchange login failure

May 14, 2007
Brian Benton sent us an update to his previous reports on the problem of Entourage clients unable to retrieve email, with a "login failure" error. Like other readers, deleting email with non-roman characters fixed the problem. But he also made an adjustment with user account permissions which affected the issue:

We seemed to have resolved the issue, but we made two significant changes.

1) Like other people we deleted non-roman spam/emails (Asian fonts in this case). This, of course, was done via Microsoft Outlook.

2) We correctly set the permission’s for the users account. The Exchange administrator noticed that the users’ permissions were not set up correctly. Actually, it appears the user had no permission to his own account, but that did not seem to cause any problems before (unless it was inadvertently changed). So I’m not sure why setting up the account generated zero errors (authentication works when setting up the account).

In any event, I would suspect other Mac/Entourage users have non-Roman email (or spam), but it does not seem to be causing a problem. So we have had no more issues like this – since we fixed the one account. We are still on the 11.3.4 patch, but should test and upgrade to 11.3.5 soon.

Read current MacWindows news here.

TIP: Automated solution for Entourage password issue, caused by corrupt non-roman fonts

Thursday, August 28, 2008

An anonymous reader provided a solution to his previous report about the problem of Entourage continually asking for a password. He previously offered a fix that worked only temporarily. His new solution is to identify email messages containing corrupt Asian-language fonts and remove them. Readers have previously identified messages with non-roman fonts as the problem, and fixed the problem by manually deleting the messages. Today, this reader offers a more automated solution...

Read entire story here

Microsoft's hotfix for Exchange fixes Entourage login failure issue

May 31, 2007

A hotfix for Exchange Server issued by Microsoft last week fixes a problem we’ve been reporting regarding Entourage login failures, according to a reader. Microsoft Knowledge Base Article 935973 describes the hotfix as the solution to a problem with Outlook Web Access (OWA) for Exchange Server. In this case, OWA users can’t read email messages that contain a mixture of Japanese and roman characters in the subject line. Users who try get an "Access is Denied" error message.

The issue we’ve reported with Entourage somewhat different. The user is prompted for a password, which is rejected, prompting the error message "Login failure: unknown user name or bad password."

There are similarities between the Entourage problem and the OWA problem that the Microsoft hotfix addresses. The Entourage problem seems to be caused by non-roman characters in email (spam) messages. Readers have reported success when deleting email with non-roman characters. The other similarity is that Entourage and Outlook Web Access both use the WebDAV protocol to communicated with the Exchange Server.

Shane Palmer said that new hotfix does indeed fix the problem with login failure problem with Entourage:

I have many users that were having the Entourage/Exchange login problems described on the MacWindows Entourage page as well and have had a trouble call in with Microsoft for several months. Our issue was narrowed down to specific Spam messages with Japanese characters in the subject field. The problem was found to be with the Exchange server and not Entourage. Microsoft released an official hotfix to patch Exchange 2003 for this issue.

Further information can be found at Knowledge Base Article 935973.

June 6, 2007
Alex Passey confirmed that hotfix works:

This hotfix works! I’ve been battling this issue for the last past year. Users are now able to login properly.

If you've installed this hotfix if it fixed the Entourage login issue.

Reader verifies hotfix for Entourage repeatedly asking for password

Thursday, May 1, 2008

Chris Johnson in London reports that a hot fix for Exchange Server fixes a problem with Entourage repeatedly asking for a password. We reported this fix before, but we thought it worth repeating:

Having tried all the suggestions of entering the domain name differently, emptying Trash etc, I still had this "unknown username or bad password" error appearing. Entourage would continue to sync for a few minutes then disconnect. I stumbled across an Exchange Server hotfix, which seems to have fixed the problem for the Entourage users.

TIP: another approach to the Entourage login problem

August 8, 2007

The above recent Microsoft hotfix solved a problem with Entourage login failures with Exchange Server, but for those who don’t like to install hotfixes, Cliff Berger has a workaround:

I too have had this login problem on occasion with the Exchange Server running Window SB 2003. I am running Entourage 11.3.3 on a MacBook OS 10.4.10, but the problem also happens with older machines and older versions,

I tend to shy away from patches such as these. I am just waiting for the new version to arrive and see if some of the issues that we have will be resolved. In the meantime, my method takes very little time and I don't have to worry about how the patch might affect other things on the computers.

The fix I have used successfully on three occasions now is to spoof Entourage into looking for a different exchange server. I did this by going to Account Settings, Exchange, open an account and change the exchange server to a fictitious named server. If you have more than one account, then you must do this for all the accounts.

Quit Entourage. Then restart Entourage. Open each account again and change the exchange server back to the correct setting. Close Entourage. Restart and you should be good to go.

TIP: fix for Entourage/Exchange login error

Tuesday, July 29, 2008

Sergio Castillo sent a fix for a previously reported problem of Entourage login failures with Exchange Server:

I just spent two days troubleshooting Entourage from Office 2008 on my Mac 10.5.4 communicating to an SBS 2003 server running as a virtual "Guest" OS on a Windows 2008 server. With enough digging around and different queries I located the solution to this problem. On my SBS Server 2003, I noticed Security Event Logs: Logon/Logoff

Event ID 531 Reason: account currently disabled User Name: GUEST NtLmSsp Workstation name: myMAC Source Net Address:MyMac's IP

Well, I started thinking that the Mac doesn't quite tie into AD like a Windows machine. I also noted there were no other errors as if Entourage never reaches Exchange. Try this:

  1. Disable Windows 2008 firewalls on itself and virtual OS it was hosting
  2. Run ADSIEDIT.msc (KB article 326690, change dsHeuristic to 00000002) This allows Guest authentication to the DC to query info, does not enable the Guest account in AD
  3. Sync your Mac. You must make sure that DNS is still working fine. I used https://localservername.internalNetBIOSname.local/Exchange/ as my server name, then my network username by itself, no domain info appended to it. Domain name was the NetBIOSname.local. If you must sync from the outside, make sure you use your external DNS name of course and make sure you can reach the same exact resources with a web browser to test authentication is okay and your URL is working fine along with DNS records.

I truly hope this will help others. I spent so much time on this and found many looking for solutions but the solution was a Microsoft Exchange Hotfix, which only fixes OWA issues with the Mac.s

If you've tried this

Another cause of Entourage password problems: large attachments

Thursday, August 28, 2008

Adam has another theory on what causes Entourage to keep asking for a password. He reports that a large email attachment can prevent Entourage from accepting your password:

I've found that if Entourage keeps asking for your password if you're already logged in. It is 9 times out of 10, a large attachment that entourage is choking on downloading from the server. Usually I will log into OWA and download the attachment local or delete the email.

If you've seen this

Elsewhere in today's news, a reader offers a procedure to fix this same problem that involves email messages with problematic non-roman fonts.

Exchange preformance degrades with large numbers of Entourage clients

April 11, 2007

Robert Liebsch, an IT Manager with a large set of Entourage users, reports that his 75 Entourage users are taxing the Exchange server, causing performance problems. He sent us an article he wrote that looks at the technical issues involved. Based on some analysis, he offered this observation:

I think MS implemented WebDAV in Entourage in a way that isn't jibing with Exchange 2003. I don't think the volume of data, number of Mac users on Exchange, etc, were thought through. I would guess that not only are Mac users suffering, but Windows users are seeing degraded performance.

He also offers some strategies for dealing with the problem. You can read Leibsch's article here along with reader responses that include links to Microsoft's KnowledgeBase and some suggestions.

Removing Entourage attachments on Exchange Server

May 4, 2007

Luis Antezana described how Entourage's Remove All Attachments only works on local email, not email stored on Exchange Server. He also gives a provided a workaround:

I just discovered to my disappointment how an Entourage feature works for accounts hosted on an Exchange server.

At the bottom of Entourage’s Message menu is a useful command called Remove All Attachments. After running the command on a selected message the attachment is removed and a History is attached to the message indicating so and when. You can’t select an attachment in a message and use the Remove button like you can with messages on an IMAP mail server, so Remove All Attachments is your only shot.

We’ve been using Remove All Attachments in hopes of reducing the amount of space that archived messages with attachments are occupying in folders in mailboxes hosted on our Exchange server, but haven’t seen the expected decrease in folder size after completion of the command. The folder size persists through a Synchronize Now command on the folder as well.

Apparently, Remove All Attachments is just for the locally cached version of those messages. If the message exists on the Exchange server, that attachment is actually still on the server, still attached to the message. It would seem the point of Remove All Attachments for Exchange-hosted accounts is simply to decrease the burden on the local Entourage database, NOT to remove the attachment from the actual message on the server.

In fact an Empty Cache command on the folder will bring back the messages intact with attachments, and that’s how I realized what was going on. Verifying the messages still have attachments using OWA is another way to see they’re still there.

The only way you’re going to be able to successfully Remove All Attachments from e-mails on an Exchange hosted mailbox using Entourage is to move the e-mail to a folder under Folders On My Computer, and execute the command there. Of course once the mail is in Folders On My Computer you can’t access it remotely through OWA or a remote e-mail client. Maybe this works differently if you’re using OWA on XP or Vista, or through Outlook, not sure.

We need to be able to delete attachments. Let’s hope this is improved in Entourage 2008.

Does this procedure work for you?

Reports of problems/fixes with Office/Entourage 11.3.5 update; Entourage, Excel disappear

May 14, 2007

A reader named Deetjen couldn’t open Office documents or install software after last week's Microsoft Office 11.3.5 update, but a reinstall eliminated the problem:

Last night after I installed the update I began encountering several problems. First, I was unable to open any Microsoft document or program. Secondly, I was unable to install any new programs (i.e. AOL Instant Messenger). I am an advanced Windows user who recently switched to Macs (15” MacBook Pro with all the goodies).

The quick fix for this problem was to reinstall the Office update. After that, everything went back to normal.

Discussion boards around the web are reporting instances of the Entourage application disappearing after installing the 11.3.5 update. For instance, see this thread at

Of this problem, Dan Pearson remarks:

I've read that the update can cause Entourage to disappear. I consider that a very important improvement...

May 16, 2007
Paul St-Pierre responded to Monday’s report of the Office 11.3.5 update causing the Entourage application to disappear. He also had other problems with Entourage and the other Office apps:

My Entourage problems occurred with the upgrade for Office 2004.

I first lost everything I had on Entourage (files, addresses, even trash) Then later, I could not print any files with either Entourage, Word, Excel or Power Point. In my 20 years with Mac, I never got anything close to this.

I spent quite a lot of time visiting sites to benefit from users' chatting on similar experiences, but didn't go anywhere…

So, with an iMac (3 months old), Mac OS X 10.4.9, Office 2004 (brand new), the student version. I upgraded to 11.3.5 and then wasted 2 full days. To fix it, I had to rebuild the computer. It now works. I however lost some software because the sellers probably think I'm freely installing this on other computers.

Conclusion: I will now be quite late in upgrading Office again.

If you’ve seen these problems with the new update

A case of all Office apps vanishing with 11.3.5, not just Entourage

May 21, 2007
Patrick Spargur said all the Office apps disappeared:

We went through a similar issue with our Mac, but the update deleted EVERY Office application. Interestingly though, when we re-installed the software from the original disks, and then ran the update again, all her emails and original docs were unaffected.

This whole thing caused a lot of fun around the house when I told her it would be virtually impossible for a software update to delete all her applications.

Spargur appears to have been correct, for if one checks the definition of “virtual,” one would see that “virtually impossible” means that it is indeed possible…

More 11.3.5 disappearing Office apps & Entourage issues

May 23, 2007
Jeremy Matthews is experiencing Entourage hanging on multiple Macs:

We just had a Mac "lose" its copy of Excel after the 11.3.5 update. And, we're seeing additional Entourage hanging/crashing on both PowerPC and Intel Macs after the update as well.

We've put out notes to all clients to NOT install the 11.3.5 it causes some serious issues!

May 23, 2007
Bill Vader saw Entourage and Excel disappear, but fixed it:

I had one on Friday. A Mac OS X 10.3.9 client used Microsoft AutoUpdate to install the new patch and lost both Excel and Entourage. I reinstalled the entire suite and re-updated from a downloaded patch and it worked fine.

May 23, 2007
On Monday, we reported that a user saw all of the Office apps to vanish. Two more readers are also seeing this. Al Keller:

Yep, after the 11.3.5 update, all Office apps mysteriously disappeared!

An anonymous reader saw this on several Macs:

A case of all Office apps vanishing: I had the same calls with all Office for Mac apps vanishing with the new upgrade. I had to uninstall the apps and reinstall them.

TIP: enabling AD users to establish accounts with Exchange 2007 and Entourage

August 22, 2007
Jeffrey Sheldon had to add some folders to Exchange 2007 Server in order to get Entourage users accounts established on an Active Directory network:

I will gladly share this headache that occurred to our organization.

Exchange Admin created a new Exchange 2007 with Rollup 3 applied to a new server. Active Directory users assigned to that Exchange 2007 Server were unable to establish their accounts via Microsoft Entourage 11.3.6. Any combination of trying to enter the account information would result in very bland, useless generic errors:

"The action could not be completed. HTTP error. The resource is not found" and "The action could not be completed. An unknown error (170) occurred."

After contacting Microsoft, it was found that the installation of Exchange 2007 Server did not have the legacy applications installed. Nowhere is it stated (or where we could find) that "Legacy Applications" includes Entourage since it is using the WebDav component that is de-emphasized in Exchange 2007.

In the IIS Administration for Exchange 2007, the virtual folders under the Outlook Web Access website did NOT contain the following folders:


Using the Exchange 2007 Shell tool, our Exchange Administrator added these folders to the website and we are now able to connect to Exchange via the Entourage clients. The wizard defaults in all the information and other than checking 'secure SSL' it works flawlessly.

I figure I could save someone $245.00 by sharing this.

if this works for you.

Office 11.3.6 update deleting Excel

August 29, 2007
Craig Brozinsky reports “Microsoft Office 2004 For Mac Update 11.3.6 deleted Excel from my computer.” This is a problem that readers previously reported with the 11.3.5 update. If you've seen this problem

Another case of disappearing Excel

Thursday, September 6, 2007

Winston Mar responded to our reports of Excel disappearing when updating Office 2004:

Same thing happened to me last week when I updated Office 2004. This was with the 11.3.6 update.

We've also had reports of this problem with the 11.3.5 update. (The current update is 11.3.7.) Several readers have also reported no problems with updating.

(Read current news on the MacWindows home page)

Entourage time zone problems with printing calendars

Monday, September 24, 2007
Chris Phelps reports printing problems printing calendars when users are in different time zones:

Weekly calendars don't print correctly for meetings set up in time zones that are not local. If someone in the EST time zone sets up a meeting from 1:00-2:00 it shows up correctly in my on screen calendar and on a daily printed calendar as being from 11:00-12:00 MST. If I print a weekly calendar, the meeting shows from 11:00MST - 2:00MST. It looks like it is simply not adjusting the time zone for the ending time. When colleagues in Europe set up meetings my calendar is a mess since all meetings appear to be at least 9 hours long.

If you've seen this problem

(Read current news on the MacWindows home page)

TIP: Entourage password problem caused by proxy settings

Thursday, October 11, 2007
Shan Younker sent us a tip to fix an Entourage password problem with a few Macs:

I used to have problems with Entourage asking for a password 2 to 3 times. Entourage was trying to log into our proxy server. I spoke with a Microsoft rep at MacWorld and he gave me a tip. Once I set up my network preferences to "Bypass proxy settings" for our internal domain, Entourage stopped asking me for multiple passwords. If only some of your computers are having the issue, make sure your account settings in Entourage match and your Network preferences match.

If you've seen this

Reader problem with Entourage inbox syncing, other MS Office issues with Tiger 10.4.11

Wednesday, December 12, 2007

Larry Fitzpatrick is having problems with Mac OS X 10.4.11 and Entourage, Word, and Excel:

I am using Mac OS X 10.4.11 and office 11.3.6 (070618).

Issue 1: Entourage won't synch the inbox at all unless the cache is flushed before the synch. That is not a guarantee of reliability however, if the cache is flushed, synch is still very flaky. Sometimes it won't synch at all, sometimes it partially synchs, and rarely it fully synchs.

Issue 2: Word will only open one document. It will not allow the item to be edited, and many menu bar items are gray. It nags many times that “Word cannot create the work file. Check the amount of disk space your startup disk.” The startup disk has 20+ GB free. Once the nagging stops, the document is frozen and will not allow scrolling (so it is not even a sufficient viewer).

Issue 3: Excel will only allow one workbook open at a time.

If you've seen these issues

Entourage syncing problem requires flushing cache

Friday, May 30, 2008

Erling Maartmann-Moe in Oslo, Sweden, is seeing the previously reported problem of Entourage not syncing the inbox unless the cache is flushed before the sync:

I am experiencing this on both my Macs. It started almost simultaneously on both machines, running Entourage 11.4.0 and OS X 10.5.2 I suspect it may have to do with size? My Outlook system is rather big, close to 2 Gig.

If you've seen this problem

Reader says Entourage is missing some email with Exchange 2007

Wednesday, December 19, 2007

Skip Sorrentino's Mac users aren't getting all of their email with Entourage:

We are a K-12 institution in Maine that uses Macs in a primarily Active Directory environment. We have recently upgraded the Exchange Server to 2007.

What we have been finding is that some of our users are finding mail in Outlook Web Access (OWA) that has not been delivered to the Entourage Exchange account, set up as an Exchange account with the OWA server.

I have done a test, by setting up that user's account with IMAP, and all the missing mail gets delivered.

We do not want to go this route, because we then loose the calendaring function, being saved on the server & not being able to have the same interaction we have come to take for granted.

If you've seen this problem

Current news at MacWindows home

TIP: Workaround for Entourage/Exchange 2007 problem synching mail

Monday, December 31, 2007

Jeffrey Berman is also seeing the problem of Entourage failing to receive some email from Exchange 2007. He also discovered an error on the server and offered a workaround:

Yes, I can confirm this problem. What is unsettling is that the Exchange Server 2007 does not sync all received messages with Entourage 2004.

I can see certain messages in the inbox folder if I access the account using Outlook Web Access or use Outlook on a Windows machine. But these messages are never delivered to the Entourage inbox folder for the Exchange account.

The only way I have been able to get the problematic messages to appear in the inbox folder of Entourage is to use Outlook (or Outlook Web Access) to move the messages to another folder and then move them back to the inbox. Of course, this means I must periodically check the account with Outlook or Outlook Web Access to see whether there are undelivered messages there.

My Exchange Server administrators have taken a look at these undelivered messages and found that the database of the Exchange server has marked them with a "mapi_e_not_found" error and this apparently prevents Entourage from downloading them. When such messages are moved to another folder, the Exchange server strips off this error message and they can then be downloaded by Entourage.

Ironically, one class of messages that have been arriving with these "mapi_e_not_found" errors is the Entourage-Talk digest!

If you've seen this issue

Tip: Another Workaround for Entourage/Exchange 2007 problem synching mail

Wednesday, January 2, 2008

Tim Levin suggests a workaround for the problem of Entourage failing to receive some email from Exchange Server 2007. On Monday, we published a workaround from another reader. Here's is Levin's suggestion:

I've seen this problem before. Two fixes. You can rebuild the users database and 40 percent of the time, all mail will show.

The best solution is to quit Entourage, delete the users local entourage e-mail database file (found in /Users/[username]/Documents/Microsoft User Data/Office 2004 Identities/Main Identity/). Then launch Entourage and enter the user settings for the account. A new database file is created and will sync with the server.

CAUTION: If the user has local e-mail stored, it will be deleted when the database file is deleted. You can save local e-mail messages by opening the folder in entourage, drag the e-mails to a folder in the Finder.

If you've tried this if it worked for you.

Current news at MacWindows home

Entourage syncing problem requires flushing cache

Thursday, July 3, 2008

Steve Fevold reports having the problem of Entourage not syncing the inbox at all unless the cache is flushed before the sync:

I've have a client who has two Macs with Entourage 2008 that won't keep the Inbox sync'd with the Exchange 2003 server. If he empties the cache for the inbox, it will update but it won't continue to update. He's convinced it's a problem with the server but I'm leaning more toward Entourage or maybe the size of his mailbox. What's odd is the other folders that he's created along with the Sent Items sync fine. The Sent Items folder has more that 22,000 items in it, that take awhile to sync up from scratch. Everything works fine using OWA or Outlook 2003.

I saw the suggestion by Tim Levin on January 2nd regarding two fixes for Entourage\Exchange 2007. I've been prompted to rebuild the database once, so I've been forced to try Tim's first suggestion. I haven't asked the user to try Tim's "best solution" of deleting the local database. I was a little reluctant for two reasons: This wasn't Exchange 2007 and it's going to take forever to sync those folders again. I'll give it a try, though, since I have no other choice right now.

If you've seen this problem

Current news at MacWindows home

Another report of Entourage 2008 Inbox not updating

Monday, July 7, 2008

Mark Richman reports having the problem of Entourage not syncing the Inbox:

I've had this same problem with Entourage 2008. The only solution I've found is to create a whole new Entourage identity. This has happened to me twice and is quite annoying. When you create a new identity you lose things like categories set on emails.

I opened up a ticket with MS on this issue. They told me that since this is with an Exchange server it must be an exchange issue and closed the ticket. Sigh.

If you have a suggestion

Tales of Entourage woe with v.2008 and Leopard 10.5.4

Monday, July 7, 2008

Brad Schrick reports having Inbox syncing problems with the latest versions of Entourage 2008 and Mac OS X, as well as several other problems:

There have always been issues with Entourage (and less so with Outlook also, bear in mind), but this has been very painful.

After the Office 12.1.1 update and the Leopard 10.5.4 update, two Macs have had mailbox sync issues that required hours of troubleshooting and recovery. Also, prior to the update another machine simply stopped updating its Inbox (meaning Entourage 2008 on each machine).

Outlook Web Access (OWA) direct from the Exchange server verges on instantaneous, and has been for years.

Entourage access to the same data has been grotesquely glacial, with frequent problems. Further, the avenue of communication for Entourage is OWA, so delays and problems in Entourage that are not in OWA are not acceptable.

One pre-10.5.4 machine (Entourage 2008) just stopped updating. Choosing mailbox properties and 'empty cache' fixed that. That user has a few dozen messages in his in box, it fixed it instantaneously.

Another machine reported that it couldn't read the database, and that user tried to rebuild, with no change. In his case, the Exchange server account got corrupted and near empty, and a backup was required. Time Machine restoration of Entourage state only ended up with that good state getting trashed by Exchange. Great logic.

Then yesterday, one message of mine was corrupted with another message. There is no 'fix this message' choice or 'synchronize just this message' in any dialog I have found.

So I tried to rebuild the whole mailbox (6000 messages) after archiving 12000 messages using another machine.

It froze Entourage twice, told me to quit, etc.

Eventually after force quitting Entourage 2008 12.1.1, fixing disk permissions, etc, it came up with a blank In box, and a blank archive box. It then proceeded to fill the In box with a large fraction of the messages I had archived--and no others. It does not fill the In box with most recent messages--man!

It took more than 24 hours to correctly fill/unfill/sync the In box with 6000 messages, and the archive with 12000.

Other than that, no problems.

Schrick then added:

By the way, when is Entourage going to STOP throwing away outgoing attachments? Entourage 2004 would do this repeatedly, with the outgoing message stuck "on my computer," where I never look. Entourage 2008 has yet to successfully send 3 separate attachments at the same time for me. I've seen this behavior over and over again, yet have not seen it reported--could it just be me? The current dialog indicates that Entourage is in a very sick state when this happens. This is insane, it's been 5 years!

If you'd like to comment

iPhone problem with Exchange Server and workaround

Monday, January 14, 2008

This article has been moved to the MacWindows iPhone and Exchange Tips and Reports page.

Current news at MacWindows home

Win Mobile bug in Entourage 2004 still in Entourage 2008

Tuesday, February 5, 2008

Richard Kingsley reports that a known bug in Entourage 2004 is still present in Entourage 2008:

Just thought I would let people know that a known bug in Entourage 2004 is still present on Entourage 2008 where the Header for items sent by a Windows Mobile device (or indeed any Exchange activesync device) are not shown in the SENT folder in Entourage.

See Microsoft Knowledge base article 926521.

Pretty annoying bug and pretty poor it was not fixed. (Only cost me £300 to find that out!)

Current news at MacWindows home

Readers unhappy with Entourage 2008 lack of Palm syncing

Wednesday, February 20, 2008

Several readers wrote to say that syncing with syncing with Palm is less than adequage with Entourage 2008, which no longer has a Palm conduit for direct syncing.

One reader described why Palm's syncing through iCal is a problem:

Entourage 2008 has missing categories. The new feature, to sync the PD indirectly via iCal and Address Book is useless when having contacts and appointments with categories. The categories are still correct in iCal, however no appointments are synced, because the calendar "Entourage" is empty. The contacts appear in Entourage without categories.

Carol Ott is considering backgrading to Office 2004:

I just upgraded to Office 2008. And I own (and live and die by) my palm. I'm astounded at what my syncing has become. What used to take a few seconds, now takes forever. Microsoft just has to correct this. Why would business users put up with this? This could be the reason why office 2008 is dropped from my company.

Thomas Michel, who also isn't happy about Palm syncing, also doesn't like Word's default .docx format:

Office 2008 is a big step backwards as far as I can discern. Files saved as Word 2008 can't be read by other users who haven't yet "upgraded", and there are even problems with files saved as Word 2004.

The loss of connectivity between Palm and Entourage 2008 is nothing short of outrageous, and reflects an enormous step backward in connectivity. A third-party solution (Mark/Space's Missing Sync for Palm OS 6.0.2) crashes every time it starts up on my computer.

I am running Mac OS X 10.5.2

(We note that users can set Word, Excel, and PowerPoint so that documents are created in the older file formats by default.)

your comments about the cross-platform capabilities of Office 2008 and Entourage 2008.

Current news at MacWindows home

EEAO 1.1 automatically moves email from Exchange to local Mac

Sunday, April 14, 2008

Last week Softhing released Entourage Exchange Accounts Optimizer (EEAO) 1.1 (US $15). The utility automatically moves older email from an Exchange account to the user's Mac, replicating the structure within Entourage. The purpose is to prevent the Exchange mailbox from getting full. Users can set how long mail is to reside on Exchange Server. EEAO can handle multiple accounts, and version 1.1 now allows users to define which Exchange accounts to process. Softhing said that the maintenance update also includes a number of "internal improvements."

Entourage issues with meeting room booking on Exchange 2007

Monday, May 19, 2008

Neil Potter in the UK described some Entourage problems with booking shared resources on Exchange Server:

We have an Exchange 2007 SP1 Server, and a mixture of Outlook 2003 and Entourage 2004 users, and some Entourage 2008, on Tiger and Leopard. We use the resource calendars for our meeting rooms and most of the time everything is okay, but we sometimes have issues where an Outlook user can either add an entry to the meeting room, by booking it manually rather than inviting it, and once done for say an hour or two. Some of the time, this booking only shows for half an hour on the Macs, but shows for the full time on the PC's.

We also get issue where if a booking has been dragged to another day on a PC to be moved, it may not show on the mac calendars. It's not every time and I'm scratching my head as to why as people seem to be adding entries correctly.

We also sometimes get SME email not showing in the inbox, which shows fine in OWA. It normally tends to be non-delivery-type emails, but worth noting I guess.

If you've seen this issue

Reader Outlook Web Access Inbox problem coincided with MobileMe snafus

Tuesday, July 29, 2008

Brian Godwin's Outlook Web Access Inbox doesn't display since he activated Apple's MobileMe service:

I don't know if this is tied to "MobileMe" but ever since the MobileMe activation (maybe purely coincidental) I cannot display the Outlook Web Access Inbox. All other functions work: calendar, tasks, contacts, but the Inbox is nothing but a blank frame. I have tried and get the same result with Opera, Camino, Firefox, Safari and even IE 5.2 However, when I load up browsers under Windows (separate computer), it works fine.

I don't know if this is a browser (doesn't seem likely), an OS, or an application issue. As I said, the only change I have made was the MobileMe conversion, which was basically back-end.

I have both of my Macs on 10.5.4 One is a PowerBook Ti 550 the other is a 2GHz iMac 17".

If you've seen this problem

MobileMe has been plagued by problems since its launch and conversion from .Mac early this month. Several weeks of problems including outages and slow response has caused Apple to give customers a free 30 days. Apple has also backed off of its initial claims of push email for Macs, and is not longer calling the service ?Exchange for the rest of us.? Apple had an email outage for over 5 days, and last week, Apple also admitted that it had lost some customers' email.

Exchange performance degrades with large numbers of Entourage clients

Reader Question of the Day: how to move Outlook email to Entourage

Monday, October 13, 2008
John Olmstead asks:

I am trying to export my Outlook mail messages into Entourage. I thought that since these are both Microsoft products, it would be a straightforward process. My mistake.

The only information I can find on either the Outlook or Mactopia sites references an MBOX file format that both Outlook and Entourage allegedly support although neither program has this format listed in the file tab for exporting or importing information.

This can't be as difficult as Microsoft is making it out to be, can it?

A: It can be, but doesn't have to. The easiest method is to use an inexpensive utility called Outlook2Mac (O2M) from Little Machines. It will move email, contacts, and calendar appointments Outlook for Windows to your Mac's Entourage, Apple® Mail, Address Book, iCal, or other Mac OS X programs.

The O2M software runs in Windows, lets you select what you need, and exports the data to files in a variety of formats (including the .mbox format) that you can import to Entourage and the other Mac programs.

Reader Entourage/Exchange problem syncing email and contacts

Monday, October 20, 2008

Richard LeSavoy cannot sync email and contacts:

I have recently set up Entourage 2008 to synch with my work Exchange 2003 server. I get a perfect synchronization in the calendar (both ways) but e-mail and contacts do not sync. I can successfully send mail from Entourage via the exchange Server but cannot receive it. I am stumped.

If you've seen this problem

Reader can sync Entourage/Exchange email but can't receive mail

Tuesday, October 28, 2008

Ryan Taylor responded to a previous report of an Entourage problem with syncing email and contacts with Exchange Server. Taylor's problem is some different, in that he can sych but cannot receive email on one Mac:

I experienced this issue last week on a white MacBook 13", OS X 10.5.5, Office 2008 12.1.3, Exchange 2003 Server. I synched up on my company's internal open, wi-fi, no proxies. Everything synched up just fine, including calendar, contacts, and email. After that, I could send email but not receive any new mail. On my Mac Pro, OS X 10.5.5, Office 2008 12.1.3, connected over Ethernet on a secure LAN, everything works fine. I can send, receive and sync. The only difference is I have an additional POP and IMAP account setup on the MacBook. The Mac Pro is strictly Exchange.

If you've seen this problem or have an idea on how to fix it

TIP: Workaround for Entourage/Exchange problem syncing email and contacts

Thursday, October 30, 2008

Justin Beek offered a workaround for problems with Entourage 2008 syncing email and contacts to Exchange Server:

I have run into this issue a lot lately. I have yet to figure out what magic key is needed to invoke it. Basically, either the local mail folder cache or the server's mail folder isn't communicating correctly.

The easy fix:

  1. Right-Click on the Inbox for the Exchange account.
  2. On the General tab, in the Empty Cache section, click Empty.
  3. It will re-download all the messages and hopefully reset the issue.

The hard fix:

  1. Rebuild the account from scratch.

If you've tried these fixes

Entourage 2008 syncing email to Exchange Server: a problem with the workaround

Wednesday, February 4, 2009

A reader named Shihabudheen is having the previously reported problems with Entourage 2008 syncing email and contacts to Exchange Server. The previously posted tip works, but is cumbersome:

I use Entourage 2008 on my Mac, syncing with our hosted Exchange Server 2003. I also occasionally use a PC Outlook client. I am able to send and receive mails from both Entourage and Outlook. The problem I have is any changes I made to inbox messages on the PC client does not get reflected in Entourage. I've tried "synchronize now" for Entourage inbox, but there was no effect. I successfully used both techniques (emptying the cache and rebuilding the account) that you mentioned in the tip Workaround for Entourage/Exchange problem syncing email and contacts.

But the problem is, to sync a single message I need to empty the whole inbox cache. In my inbox there are many messages. Is there any easy way to sync a single message? I found something like changing message's "connection status" to "download at next connection" using Applescript but it was also not working.

If you've seen this or know the answer

TIP: Reader traces fix for Entourage/Exchange 2007 mail synching problem to Win 2008

Friday, November 14, 2008

Howard Wanderman adds to the discussion about the problem of Entourage failing to receive some email from Exchange 2007. We have several workarounds listed, but Wanderman recommends a permanent fix:

I came across this and it fixed my problem with certain emails not showing up in Entourage on Exchange 2007.

It turns out that:

a) It's actually Windows Server 2008's fault. (More specifically, the included IIS 7 build), and

b) The specific emails that are not appearing contain potential escape characters in the subject field, posing a security risk.

There's an article on this here.

The short of it is that allowing IIS 7 (which is what serves up HTTP to Entourage) to allow these characters will thus allow it to pass them along to Entourage.

If you've tried this approach

Reader's Entourage 2008 can't sync or access Exchange inbox

Monday, June 15, 2009

Allyn Martin has an Entourage user who can't see his Exchange Inbox:

We have lost ability to sync or see Inbox messages from Exchange in Entourage 2008. OWA and Outlook on the PC work fine. We are at wit's end why one user cannot access/see his Inbox items. We can see the size reported back to us with content there. I broke down the Size of Inbox to be more manageable.

Deleted Cache and all items are gone: it doesn't rebuild listings except Deleted Items, Junk Mail and 1 inbox folder containing 2 eMails from 2006 in it.

Now we are looking at permissions on the Exchange 2007 server to see what it could be. We just migrated last Thursday fine and it was working until Monday AM - then BOOM!

If you've seen this problem

Last month, we had reports of corruption of Entourage 2008 databases, though we don't know if Martin's problem is related.

TIP: Fix for Entourage 2008 can't sync or access Exchange inbox

Wednesday, June 17, 2009

Two readers responded to Monday's report about a problem with Entourage 2008 not being able to sync with Exchange Server's inbox.

Mike McCallum found a fix that involved editing the Windows Registry on the server:

We had been fighting this for a number of weeks and after many hours with Microsoft Tech Support, our Windows engineers resolved using the solution listed below.

As discussed find the below commands which helped in resolving this issue:

C:\Program Files\Common Files\System\Ole DB\Oledb32.dll
C:\Program Files\Common Files\System\Ole DB\Oledb32r.dll
C:\Program Files\Common Files\System\ado\Msado15.dll

To register a .dll file:

Click Start, click Run, and then type regsvr32 followed by the path and name of the .dll file that you want to register. For example, to reregister the Oledb32.dll file, type the following command at the command prompt:

regsvr32 "c:\program files\common files\system\ole db\oledb32.dll"

The info on reregistering dll files is also available in KB#823159 under "Reregister the MDAC Components".

If you've tried this fix

Patrick Au reported having the same problem:

I have the exact same problem, I have 2 site one works one doesn't and have this problem on and off for over 6months. The site that works has the exact same set up except the exchange server itself its a domain controller. Not sure if thats related. Tried everything like Allyn and still same problem even after clearing the OS keychain. I thought I was the only one too.

Plus character in email may be behind Entourage/Exchange 2007 sync problem

Monday, March 30, 2009

Aidan Richmond believes a plus (+) symbol may be the cause of the problem of Entourage not properly syncing with Exchange Server 2007 and missing some email messages:

Regarding your readers report on Entourage missing some messages from an Exchange 2007 server, we have recently upgraded to Exchange 2007 and from testing it seems that for us messages with a "+" symbol will not make it through to Entourage. There may well be other characters that cause the same problem, but so far this is the only one we've narrowed down.

If you've looked at this

Readers verify plus symbol in email a problem for Exchange

Wednesday, April 1, 2009

Two readers verified Monday's report about a plus (+) symbol in email being the cause of Entourage not properly syncing with Exchange Server 2007 and missing some email messages.

Augie Fusz started seeing this with Windows 2007 server:

I have seen this issue too. We upgraded to 2007 Server a few months ago. When there is a plus symbol in the "Subject" field, the messages will not sync to Entourage clients in Office 2008 for Mac. Unsure if the problem exists in office for Mac 2004.

Andy Law also sees a problem with OWA:

I don't know if it is related, but the web interface (OWA) to the Exchange server is similarly unable to access messages with a Plus symbol in them. They are listed in the messages within the Inbox in that interface, but clicking on the message in an attempt to view it just gives an error message. That's been a problem for a long time.

If you've seen this problem

TIP: Workaround for + sign preventing Entourage/Exchange sync

Friday, April 3, 2009

Two readers (Joshua Churchill and Dwight Feller) sent us a link to a workaround for the Entourage problem of not syncing messages with a plus sign in the subject. Churchill reports:

There is a work-around for the issue where messages with plus signs in the subject do not sync with Entourage when connected to an Exchange 2007 server.

Specifically the problem occurs when Exchange 2007 is running on Windows Server 2008. Server 2008 introduced IIS7 which is the where the problem occurs. The server administrator can follow the steps detailed at this link at to correct the problem.

If you've tried this tip

Two other readers report that the problem is limited to Entourage and doesn't occur with Outlook Web Access. Graham Norbury says the problem also does not occur with a smart phone:

I have been testing this morning with Entourage 2008 version 12.1.5 with Exchange 2007. An email with a '+' symbol in the subject line it doesn't appear in Entourage 2008. It does however work in the OWA interface and with mail2exchange on a Nokia phone.

I have also tested for the '+' symbol in the body of the email and that works for Entourage, OWA and on the phone. It's just the subject of the message, and only in Entoruage.

Michael Salmon:

I just tried sending a message with he subject "Test of +" and I could read it in OWA without problem, both the lite version with safari and the full version. Unfortunately I cannot test it with Entourage.

Entourage/Exchange "plus sign" sync problem: more characters involved?

Wednesday, April 15, 2009

Bob Potter has a theory on the Entourage/Exchange problem of not syncing when a plus (+) symbol is in the subject field:

We have the same issue. We cannot even read these messages in OWA. We get an error "The system cannot find the file specified."

And I think it may extend to hypen (-) and percent (%) characters as well. Our IT dept. says they think it has to do with SPAM blocking. They are hesitant to do the workaround because they said we are getting many SPAM messages that have those characters in the subject.

Recently we reported a workaround for the problem.

TIP: URLScan may be behind Entourage "+" sign syncing problem

Tuesday, June 23, 2009

Long-time MacWindows contributor Peter Kloss believes an application on Exchange Server causes the problem of plus (+) symbol in email messages causing Entourage to not syncing with Exchange Server 2007. Kloss reports:

Emails not syncing from Exchange to Entourage because there is a '+' in the subject line are usually because the application URLScan has been installed on the Exchange Server to improve the security of IIS. By default it blocks certain characters in URLs including the '+' sign that could be used to construct malicious URL strings in an attempt to compromise the server. As Entourage uses WebDAV to access Exchange (at least in Exchange 2003) all its accesses are by sending very long and complicated URLs to the Server. It is not uncommon for these to break the URLScan rules and access is blocked. OWA will show the same symptoms and here you can see an email with the '+' in the subject line but you can't open it to read -- very frustrating. Our implementation here of Exchange 2007 on Windows 2003 does not have the problem - we did not install URLScan! Looking at the IIS logs on the Server is instructive as you can see the access fail with the appropriate HTML error code.

This problem that is 'fixed' by not running URLScan will return -- if Windows 2008 is being used as the base OS for an Exchange install. This is because the default IIS 7 implementation includes a 'double escape' filter which blocks '+' signs! The reference for dealing with this is a Microsoft blog. The Microsoft Entourage Team blogs are a worthwhile read to try to decode some of these problems.

If you've tried this

Another report of plus character in email and Entourage/Exchange sync problems

Friday, July 2, 2010

Eric Pho is seeing a problem we reported (with suggested workarounds) over a year ago:

I'm experiencing the problem which occurs when I got a "+" symbol in every subject in a messages, the mail won't be received in the Entourage client, but the mail is present in webmail.

If you know of a fix

TIP: Microsoft fix for Exchange/Entourage "+" sign problem

Tuesday, July 6, 2010

Responding to a report last Friday, Brad Morris shared a Microsoft fix for the problem where Entourage doesn't receive email messages that contain a plus (+) sign in the subject:

The documented solution from Microsoft is to enable double escape characters in IIS on the Exchange Server. I ran into this when we deployed in 2008 and this solution resolved. There are security implications people should be aware of before implementing, but in our case we had no choice.

If you've tried this fix

Reader: MS fix for Entourage "+" problem didn't work, but WSE did

Thursday, July 8, 2010

Craig Pepper reports on Microsoft's fix for the Entourage problem of not receiving email messages with a plus (+) sign in the subject:

We tried the Microsoft fix, which fixed the problem for a short time but then came back. Upgrading Entourage to version 13 (the Web Services Edition) fixed the problem permanently for us.

If you've tried the Microsoft approach, or upgrading to Entourage WSE

Reader says Mac Office Update 12.1.3 doesn't fix "doesn't match IP address" bug

Tuesday, October 28, 2008

Daniel Lee reports that the recent Office 2008 for Mac 12.1.3 update doesn't fix an bug that it is supposed to fix:

Just shooting you an email to let you guys know that this update did not fix the issue of getting the "server name or IP address does not match the name or IP address on the server's certificate" error message when connecting to Exchange 2007.

I've tried deleting my profile from Entourage and setting it back up but the issue persists.

If you've tried the 12.1.3 update if you see this problem.

Another reader reports Entourage 12.1.3 doesn't fix "doesn't match IP address" bug

Thursday, October 30, 2008

Russell Tolman verified that the Office Mac 12.1.3 update didn't do much to fix the Entourage "doesn't match IP address" bug:

I see it all the time now. It came with 12.1.0 and was gone with 12.1.2. Now it is back with 12.1.3. It is not consistent in my school district.

I have deleted the entire Microsoft Data in the Documents folder and reset the account from scratch, and the problem is back. It drives me crazy.

If you've seen this issue

Reader can't sync Palm to Entourage 2008

Tuesday, February 24, 2009

Nina Rappaport reports that she can't sync her Palm Treo with Entourage 2008. With Office 2008, Microsoft dropped direct syncing of Entourage with Palm devices. Third parties have offered support, but Rappaport said that Marc/Space's Missing Sync had problems:

I have a Treo 650 and it always synced with Entourage 2004 on my Mac. I bought the Office 2008 package software and now it doesn't sync. It seems that Entourage doesn't sync with Blackberry or iPhone, too.

Marc/Space Missing Sync didn't work for me -- it doubled my entries. And it didn't sync my calendar at all. So now what I have done is sync my calendar to 2004 program but I can't work efficiently -- and I might as well hand write as in the dark ages.

I really need to be able to use my calendar on my computer, go from email to calendar appointments, and notes. I work for myself and have no tech support.

How do I sync? I now have things double up and most addresses don't sync over. I am still using my Palm. I was about to buy a Blackberry thinking it would work, but from the blogs it doesn't seem any one has that working either.

If you've seen this problem or have a suggestion

Reader can't delete email from Entourage 2008

Monday, March 30, 2009

Carson Schutze reported a problem deleting mail from multiple Macs. This reminds us of a 3-year-old problem, supposedly fixed long ago. Schutze said:

This sounds similar to problems reported on your site but not identical. After starting to access my exchange account from a new Mac running 10.5.6 (previously only used 10.4) using Entourage 2008, I started finding that messages I deleted from one Mac would show up as not deleted (i.e. not moved to the Deleted Items folder) when I accessed the same account from Entourage on a different Mac, and then would also not have been deleted when I re-accessed the account from the original Mac. Rebuilding the database doesn't generally help, and in particular does not get Entourage's version of the Inbox to match what webmail says it should look like. Likewise flushing the cache can have various bizarre effects, including making hundreds of messages disappear from the local Entourage inbox when webmail says they're still on the Exchange server. Prior to the use of this new 10.5 machine I never had any such problems.

If you've seen this problem

Another case of can't delete email from Entourage 2008

Wednesday, April 15, 2009

Andy Meng verified a report about a problem with Entourage 2008 not deleting email:

I am experiencing this exact problem. I can access my Exchange account via Outlook and iPhone. When I delete messages with either of these, they truly delete. When I delete from Entourage they don't delete from Exchange and still appear on my in box in both outlook and iPhone. If I sync my inbox on Entourage the "deleted" emails show back up. This appears to be a bug in Entourage where it's not actually deleting emails from the Exchange servers.

If you've seen this

Suggestion for deleting hard-to-delete Entourage email

Friday, April 24, 2009

Daniel Tangney sent in a suggestion for a problem deleting email from Entourage 2008:

Use the Edit>Purge Deleted Items command for emails that don't delete normally. There must be something special about these stubborn emails.

The Purge command, however, doesn't seem to always be visible. The Entourage Help system mentions the command:

Delete the messages from the server. When you delete messages from the server, Microsoft Entourage automatically removes them from the Message list. To delete messages from the server, click Purge Deleted Items on the Edit menu.

If you've tried this

We also received addition reports of the problem from readers. Kristine Campbell:

When I delete email on one Mac, they are still there when I open Entourage on the other Mac. This happens regardless of the amount of time I wait for syching between Entourage and Outlook. I feel like this is a recent problem (last month or two).

Erik Hydo also has a problem accepting events:

I am having this same problem of not being able to delete emails in Entourage. Not only am I not able to delete emails, I cannot accept calendar events either. I have removed Entourage/Office and all of the user profile files and reinstalled it. I still have the same problem.

Daniel Tangney:

Some email messages just won't delete. You can try several times but to no avail. Fortunately, you can delete most messages. Doesn't seem to be any rhyme or reason why some delete other don't.

Readers says Entourage email deleting problem affects OWA

Thursday, April 30, 2009

Harry Fahey in Australia reports a twist to a problem with Entourage 2008 not deleting email:

In response to the case reported on April 15, at our school one of our Mac users can delete messages from Entourage, but they will show up as not deleted when he accesses his Exchange inbox via Outlook Web Access. Strangely, he cannot delete items from Outlook Web Access until they have been deleted from Entourage first.

If you've seen this issue

Another report of Entourage problem deleting mail

Wednesday, May 13, 2009

Ivan Drucker is having the problem Entourage 2008 not deleting email:

I've observed the same thing others have, at least with whatever version of Exchange Server Intermedia is using. I've seen it on both our clients' accounts and my own. If you delete a message in Entourage, or change its flagged status, it looks fine in Entourage but the change doesn't actually happen on the server; this is easy enough to see by using webmail. (If you delete it in webmail, however, Entourage does get the change.) I don't know how long this has been going on, but I think a client first reported it to me at least a couple of weeks ago.

Of course, any other devices (other computers, iPhone, etc) are similarly affected. Precise steps to reproduce: open Drafts folder. Save test message into Drafts. Synchronize now. Look at web mail, verify that it shows newly created test message. Delete test message in Entourage.

I have verified this in Entourage 11.4.0 (2004), 12.1.5, and 12.1.7. I haven't tried other versions, but the fact that it happens in both 2004 and 2008 makes me suspect the Exchange server. In any event, it's very frustrating.

If you've seen this

Entourage problem deleting email continues

Monday, June 15, 2009

Gazz has the problem of deleting email from Entourage, sometimes:

I have started having the same problem about four weeks ago. But interestingly it seems to depend on where the mail comes from. From individuals, it seems to delete. But my work mail from the company server will not. I thought that it was something that they had done until I saw this post.

If you've seen this problem

One more report about Entourage email not deleting

Tuesday, July 21, 2009

Elizabeth Hinkle-Turner reports having the problem with Entourage email not getting deleted:

I have the same problem. I delete items in Entourage and yet they are still there in Outlook.

The only suggestion we've received so far is this: "Use the Edit>Purge Deleted Items command for emails that don't delete normally."

If you know of a workaround

Handling Entourage 2008 database corruption, lost email

Monday, May 18, 2009

John Underhill is having frequent corruption in Entourage databases, resulting in losses of thousands of email messages. He found he could recover them from Exchange Server using Microsoft's PFDAVAdmin:

Our Entourage mail databases routinely become corrupt, resulting in bizarre behavior in Entourage, or warnings from Entourage that its database is corrupt. Rebuilding the database sometimes helps, sometimes not...

Read entire story here and more reports of this problem

Reader reports duplicate syncing with BlackBerry with Entourage

Monday, March 8, 2010

Chris Wood reports problems syncing a Blackberry smart phone with Entourage 2004 and 2008. Every 8 hours, he winds up with duplicate calendar items:

I recently upgraded my BlackBerry to a Curve 8900 which required me to use the new BlackBerry Desktop Manager for Mac. In exploring this sync problem with BlackBerry they concluded that it was between the OS (Snow Leopard) sync services and Entourage. At the time I was using 2004, which was not universal binary code and thought this was the problem so I upgraded to Office 2008. The problem still exists.

In my scenario the duplicates are exactly 8hrs apart because the OS is set for Pacific Time which is GMT+8hrs. Entourage is also set for Pacific Time but it does not allow you to specify a time source. You would think it would be the OS time source but this does not appear to be the case. It seems to be taking the OS time and then calculating the time zone variable on top of it which in my case adds another 8hrs.

In iCal if I use my home calendar as my base with the entries and then enable the Entourage calendar the duplicate entries are added with the 8hr difference. If I sync it this way and the sync services do another update them I end up with another set of duplicates 8hrs later than the last set resulting in 3 entries for the same appointment.

I have no solution to offer but it has to be in the coding of Entourage itself as my BlackBerry sync's fine when just using iCal.

If you've seen this problem

Mac OS X 10.6.6 causes Entourage to hang

Friday, January 14, 2011

Maryann Whitley reports that the Mac OS X 10.6.6 update created a problem with Entourage:

I'm running Office: Mac 2008 on a MacBook Pro. Since I updated to 10.6.6 Entourage has had problems. It boots up and loads emails but then hangs and becomes unresponsive. I have to force quit. I hope this gets fixed quickly. Here's a bit of the error log:

Command: Entourage
Path: /Applications/Microsoft Office 2008/Microsoft Entourage
Version: 12.2.8 (12.2.8)
Build Version: 0
Project Name: (null)
Source Version: 101117
Parent: launchd [541]

PID: 4763
Event: hang
Duration: 5.02s (sampling started after 2 seconds)
Steps: 10 (100ms sampling interval)

If you've seen this problem

Another readers says OS X 10.6.6 update causing Entourage hangs

Tuesday, January 18, 2011

T. Beller confirmed Friday's report that the Mac OS X 10.6.6 update is causing Entourage to hang:

Regarding problems with 10.6.6 update and Entourage, I have the same problems as Whitley, plus crashes and I have to rebuild database.

If you've seen this issue

Current news at MacWindows home

Reader reports Entourage/Blackberry/OWA time zone sync problem

Monday, February 21, 2011

Christina Hacopian finds that the time zones for appointments keep changing around when she syncs between Entoruage, Outlook Web Access, and a Blackberry:

Verizon, Blackberry and GoDaddy all point the finger to Entourage, and I don't know where to turn. When I input a calendar event on my Blackberry, it appears correctly on my OWA (Outlook) calendar, but then changes time zones on my Entourage calendar. Moreover, when I input a calendar event on my OWA calendar, it appears correctly on my Blackberry but again, not on my Entourage. It changes time zones.

It seems there is a miscommunication between the OWA Outlook calendar and my Entourage calendar. Go Daddy, my host, says the error is on the Entourage side. All of my time zones are set to Pacific (Blackberry, OWA and Entourage), however, appointments appear as Arizona time zone on my Entourage calendar.

If you've seen this problem

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