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Mavericks, Outlook, Mail, & Exchange

Tips and Reports

Solving problems with OS X 10.9, Outlook for Mac, and Mail & Exchange

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Outlook on Mavericks duplicates messages

Steven Goodman reports a problem with Outlook for Mac after installing OS X 10.9 Mavericks:

Outlook 2011 (14.3.8) is behaving strangely since I upgraded to Mavericks. It downloads multiple copies of each message. I didn't change anything in my Outlook account, which was working fine before. Someone told that POP might be the problem, so I changed the settings to IMAP. This didn't fix it. I also tried rebuilding the database but this didn't have any effect either.

If you've seen this problem .

Reader confirms Outlook on Mavericks duplicating messages

James B. in the U.K. confirmed a previous report about problem with duplicate messages in Outlook for Mac on OS X 10.9 Mavericks:

I've experienced this issue too, and it's driving me crazy. Since upgrading to OS X 10.9 Mavericks, Outlook 2011 has just started to download all of my emails for a 3rd time. I've 33,000. I'd like to keep on my mail server, but I don't want all of these constantly downloading to my Mac.

I've had to set up rules to hive off any emails downloaded with a sent date of over 30 days into a folder so I can easily delete the local copies. I've changed nothing in my Outlook settings. What's going on?

If you know what's going, or have seen this problem .

Outlook update doesn't help Mavericks Outlook mail duplication

James B. sent us an update to his report from yesterday about mail duplication with Outlook on Mavericks to say that the most recent Outlook update didn't fix the problem. He also describes how he's dealing with it:

I applied this update (Office for Mac 2011 14.3.9) after I sent my note to you, but it's had no apparent effect on this problem. I've resorted to hiving off the majority of my emails to an archive folder on my mail server -- only a short term mitigation but at least I'm only getting duplicates of the last month's emails now.

Mavericks Outlook mail duplication seen with sent mail

We have two more responses to reports of mail duplication with Outlook on Mavericks. First, Gene Steinberg, host of the Tech Night Owl radio show sees the problem, but in a different mailbox. He also sees it with OS X's Mail app:

For me it's the Sent messages box, where outgoing messages are duplicated. ItÍs strictly on the Mac under Mavericks. I set it up with ActiveSync on my iPhone with iOS 7.0.4, no problem. Just the Mac with Mail or with Outlook 2011.

The problem doesn't appear with the Inbox or any other email folders.

I posted a message on the Outlook forum at Microsoft, and someone from the company asked for more information about my setup. Maybe they want to try to fix it.

If you've seen this problem, with Outlook or with Mail, .

Brian Marsh has a few observations:

There may indeed be a bug with Outlook/Mavericks/POP, but the first person who wrote in said he tried changing to IMAP, he may not realize that this would cause Outlook to download all of the messages again since it wouldnÍt even look at the POP database for what was already there. (it is essentially a new account) So Outlook setup for IMAP would "download" (cache) all of the messages on the server again.

This problem has not reproduced on any of the Macs I have access to with Outlook 2011, Mavericks and Exchange 2007. (Not set for POP or IMAP.)

If this helps .

Mavericks duplicate Sent mail and potential Apple fixes

Robert Hancock confirmed a Mavericks problem with large duplications of mail in the Sent box, using OS X's Mail app. The problem with Mavericks has also been seen with Outlook for Mac. Hancock says: I have seen this several times. A single large sent mail appears in the Sent folder up to 20 times… (Read entire story here.)

Mavericks duplicate Sent mail with Outlook.com

Peter Holden reported an interesting twist on the Mavericks duplicate mail problems in Outlook and Mac Mail:

I have exactly the same problem (duplicate Sent mail) in Mavericks using Apple mail when connecting to the Outlook.com email service.

If you've seen this problem .

Duplicate Outlook email in OS X 10.9 can number in the 1000s

Jeff Blaine is another reader reporting receiving duplicate email in Outlook after updating his Mac to Mavericks. In his case, the number of duplicates can number over 1700. There is no known workaround except to switch to Mail. Blaine writes…(Read entire article here.)

No fix for massively duplicated Outlook email with OS X, but maybe a clue

Thomas Atkinson responded our reports of massive duplication of Outlook Mac email under OS X Mavericks:

This fiasco with getting thousands of old duplicate emails 1-2 times every single day is growing tiresome. I may just unplug my Macs (5 of them) and park them until this problem is fixed. It's really ridiculous that…(Read entire article here.)

Could virus software cause Mavericks Exchange mail duplications?

Bryan Schappel speculates that Sophos anti-virus software may behind problems with massive duplication of Exchange email with Mavericks and Outlook and Mail. He suggests a workaround if this is the case:

I do not use Outlook on the Mac but my former company used Exchange 2003 and I used DAVMail to read my mail. One of the steps in setting up DAVMail was to add the localhost (127.0.0.1) to the allowed website list in Sophos Anti-virus. The clue submitted by Thomas Atkinson reminded me of this setup.

I wonder if the people with duplicate email are running Sophos. If so, then they might want to add the Exchange server to the allowed website list. A similar exclusion might be needed for other anti-virus software.

It makes sense to me. If the AV product is interfering with the data stream during a send/receive session and this causes Outlook to redownload messages then this might be the solution.

If you've tried this suggestion how it worked out.

Outlook massive mail duplication continues with OS X 10.9.2

Bob Menna reports that the Mavericks 10.9.2 update has not fixed the problem with Outlook for Mac downloading hundreds or thousands of duplicate emails. He is also having an issue where he repeatedly must enter a password. Menna wrote: I am having… (Read entire article here.)

TIP: "Prevent App Nap" may fix Outlook massive email duplication in Mavericks

Bob Menna, who previously reported massive duplication of email with Outlook 2001 in Mavericks 10.9.2, thinks he has found a fix. This is the problem where Outlook creates hundreds or thousands of duplicate emails. Menna's fix is to check the Prevent App Nap box in Outlook's Get Info window… (Read entire article here.)


TIP: Mavericks won't sync Outlook & iPhone, but Exchange is a workaround

Readers are reporting that since updating to OS X 10.9 Mavericks, their iOS devices no longer sync calendars or contacts with Microsoft Outlook via iTunes. Workarounds are few because the problem is the result of Apple removing Sync Services from Mavericks. Sync Services was the core OS…(Read entire article here.)


Mavericks scrambling and emptying Outlook folders

Cecilia reports that since updating her Mac to OS X 10.9 Mavericks, Outlook has duplicated folders and emptied them of email. However, the folders were still available on the server via the web, but they aren't visible from Outlook… (Read entire story here.)


Mavericks 10.9.1 fix OS X email snafus but Outlook not mentioned

Apple released OS X Mavericks 10.9.1, an update that focuses on number of problems with e-mail as well as fixes for Safari and security. However, there is no word from Apple on whether the update addresses Outlook problems that occur with Marvericks, some of which are similar to those found in Apple Mail…(Read entire story here.)


Mavericks 10.9.1 problem sending with Mail app through Exchange Server

Ulrich Wesche reports that updating Mavericks with the OS X 10.9.1 version did not solve problems with duplicate mail with the Mail app and Exchange Server. He also reports that the update unfortunately introduced a new problem with Exchange: Here's what happened after the installation of the…(Read entire story here.)

Reader confirms Mavericks 10.9.1 Mail problems sending to Exchange Server

Kenny Anderson confirmed a previously reported problem with OS X Mavericks 10.9.1 sending email to Exchange Server, with multiple drafts saved. He also has problems downloading messages from the server. Anderson reports: I recently upgraded to Mavericks and Mail became very glitchy… (Read entire story here.)

More Mavericks Mail woes with Exchange Server

Three more readers reported problems with OS X Mavericks Mail and Exchange Server. Problems include not being able to send or receive mail, hundreds of duplicate draft messages (a problem also reported with Outlook on Mavericks), and blank messages dated from 1969. Chap Harrison writes…(Read entire story here.)

More on Mavericks and Exchange problems

We have two more reports on problems with Mail and Outlook and Exchange Server. One report is from a reader with the problems and another from someone not seeing the problems who thinks a version of Exchange or Auto Discover may have something to do with it. David Toub has the problems…(Read entire story here.)


TIP: Apple workaround for Mavericks Mail problem

Apple has posted a workaround for problems receiving mail with Mail in OS X Mavericks, a problem that some readers have previously reported with Mavericks Mail and Exchange Server. Apple says that no new email arrives until Mail is quit and reopened. Apple's workaround is to force Mail to reconnect…(Read entire story here.)


Reader can't access Outlook Web with Mavericks

Ali reports being unable to access Outlook web mail since updating OS X to Mavericks:

My Outlook email works terrible since installing the latest OS X. I cannot access my Outlook email from Safari or Google Chrome. When I access it from Safari, and can see who I have messages from but they will not load.

Yesterday I unplugged my modem and plugged it back in and then I was able to access my emails, very slowly. But, this morning I am back to having troubles. Depressing.

I always figure I am safe with Mac, but after the last upgrade, and now this one, the Internet and other things are laggy.

If you've seen this problem .

Reader's OWA on Mavericks issue may be server issue

Paul Gorski responded to the report "Reader can't access Outlook Web with Mavericks:" Reader-can-access-Outlook-Web-with-Mavericks.html

You have a reader that mentions he/she is having problems with Outlook Web Access under Mavericks; it works fine on three or four different Macs I manage. Safari, Opera, and Firefox (with a boat load of extensions too) all good. Running 10.9 and 10.9.1. I use OWA all day under 10.9.1. It might be the Exchange server the user is connecting to.

Both OS X 10.9 and 10.9.1 have lots of problems with Outlook and OS X Mail and Exchange Server. if Outlook Web Access is a problem for you on Mavericks.


TIP: Workaround for Outlook can't open private event

MacWindows Forum user Williamjacobs offers in a workaround for a problem not being able to open your own private calendar events in Outlook Mac. He says this happens if you share your own calendar folder. If you do, you can remove the shared calendar from view and recreate the events in the personal calendar. Read more and post a comment in the MacWindows Forum.

Got a problem or tip about OS X 10.9 file sharing?

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