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iPhone/iPad and Exchange Server Tips and Reports

Reports and Tips about using iPhones and iPads with Microsoft Exchange Server

Updated March 25, 2013


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Tips and Reports

If you’re using iPhone and Exchange about any problems or tips.


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Reader TIPS and Reports

TIP:iPhones' Deleted Items folder on Exchange disappears, and a workaround

Monday, January 14, 2008

Dave Loverink reports a problem with iPhones and Exchange Server that results in the disappearance of the Deleted Items folder. He also reported the workaround:

I wanted to pass along this information about a problem with iPhones accessing Exchange Server mailboxes. There is a partial workaround included.

We recently encountered a problem where items in a user's Exchange server-based Deleted Items folder were disappearing. One minute there would be a few hundred items in the folder and the next minute less than 20. We were able to use the Outlook "Recover Deleted Items" tool to retrieve the items. However, anywhere from a few minutes to a few hours later, they would disappear again.

We quickly figured out that this was happening on only two of our accounts - one a PC user with Outlook 2003 and the other a Mac user with Entourage 2004. Without any commonalities in the client software, we started looking at the Exchange server, but were unable to find any problems there. We finally discovered that both accounts were being accessed by the user's iPhone in addition to their desktop email client.

The iPhones were configured to access the Exchange server using IMAP. In the mailbox settings on the iPhone, under Advanced/Mailbox Behaviors, "Deleted Mailbox" was pointed to the user's Deleted Items folder on the Exchange server. Remove Deleted Items was set to Never.

It appears that with this configuration, deleting a message on the iPhone caused the Deleted Items folder on the server to be nearly emptied (it always left a few recent items, somewhere between 5 and 40).

Changing "Remove Deleted Items" to a setting other than Never had no effect on the problem.

Workaround

As a partial workaround, we created a new Exchange server folder called "Deleted From iPhone" and pointed the iPhone Mailbox Behaviors "Deleted Mailbox" to that folder. After this, items stopped disappearing from the Deleted Items folder. With further testing, we confirmed that items in the ?Deleted From iPhone? folder are now disappearing. For now, we're telling users not to delete messages from the iPhone unless they are absolutely sure they won't need them.

Version info: Exchange 2003 on Windows Server 2003 R2 SP2. Both iPhone are running v1.1.2 of that OS. These iPhones came with 1.1.2 out of the box.

Additional reports of this problem can be found at the Apple Discussion Forums.

If you've tried this if it worked.


Reader reports iPhone email to Exchange email is garbled

Monday, September 29, 2008

Michael Wilmar is having a problem with iPhone email messages sent to Exchange Server:

I am beta testing an iPhone in an enterprise environment. I use Entourage with an Exchange Server. We are using MS Active Sync technology for email on the iPhone. For some reason, email messages sent from the iPhone show up as gibberish in the Sent Items Folder on the Exchange Server and in the Sent Items Folder in Entourage after synchronization, although they look fine on the iPhone.

If you've seen this problem

Last spring, Apple announced that iPhone 2.0 included Exchange support. Apple's web site describes iPhone's support for Microsoft Exchange ActiveSync.

Workarounds for iPhone/Exchange garbled message issue

Friday, October 3, 2008

Several readers responded to Monday's report of email messages from Exchange Server that were garbled when viewed from an iPhone or iPod Touch. The Entourage Help Blog describes the problem and an AppleScript that lets you read the messages. (Thanks to Michael Wilmar, Shane Palmerm Chris Little, and Mark Richman for the tip.)

A reader who wishes to remain anonymous sent another workaround:

This is a known problem. Messages sent from an iPhone appear in Entourage's "Sent Items" folder as unformatted mime files. There is a workaround: just bcc yourself on outgoing email messages, then find messages from yourself in your "Inbox" and move them to the "Sent Items" folder. Delete the mime files by sorting by subject and they'll show up at the top of the list as <no subject>. If this workaround weren't so easy, I'd have already contacted Microsoft to address the issue.

Jason Halvorson writes:

We have seen this where I work too: Exchange Server 2003, iPhone 2.0 - iPhone 2.1, and Entourage 2004/08. The messages appear correctly in Outlook 2003, Outlook 2007, and Outlook Web Access. Apparently it's known to Microsoft as well. The header information is not displayed in Entourage 2004 for an email message that is sent by using Exchange ActiveSync.

Donald Wagner sent us a similar note:

This is a known issue with any message sent via ActiveSync and Entourage. It was an error in Exchange 2004 and was not corrected in Exchange 2008.

Sylvain Bois said the iPod Touch is not immune:

I have the same issue using iPod Touch on an Exchange server.

Erik Ableson isn't seeing the problem at all:

Just a quick note to pass on that we have 6 iPhones in the office connecting to Exchange 2008, originally with a direct port mapping through the firewall, and now via ISA server with no anomalies of this type. Currently using a self-signed certificate.

TIP: a simpler workaround for iPhone/Exchange garbled email

Monday, October 6, 2008

Erick Abad has a better workaround for the problem of of garbled email messages from Exchange Server viewed from iPhone or iPod Touch.

I have a better an easier way without have to BCC.

I added a folder in Exchange called "Sent Messages" or "Sent Messages 08". You can call it whatever you want. It's a good way to manage your sent emails from Exchange by creating folders per year or quarter if you wish. In Entourage, I have a rule to move sent messages to my Sent 08 folder automatically when I compose mail on my desktop.

On my iPhone, I just mass select the emails I've sent from the iPhone in the "Sent" folder and move them to the "Sent Messages". For some reason, moving email from Exchange through the iPhone to one of the folders reverts the emails to normal. It's no longer unformatted mime files. Headers, subject, formatting is all there.

If you've tried this

Tip for iPhone/Exchange garbled email doesn't work for reader

Thursday, October 16, 2008

Our most recently reported tip (directly above) for fixing the problem of garbled Exchange email viewed from iPhone doesn't work for Eric Bohner. He didn't elaborate, or say if he tried the other suggestions on our.

Confirmation of fix for iPhone/Exchange garbled email

Monday, December 8, 2008

Glenn I. Fishman reports "I just tried this tip [Oct. 6] for the iPhone/Exchange garbled email - it worked great."

The problem is described here. If you've tried this or the other fixes listed

Reader: workaround for Garbled iPhone, Entourage doesn't work

Friday, June 5, 2009

Antony Harris says that the previously reported workaround doesn't work for a problem with garbled email in iPhone, Entourage and Exchange:

I am also experiencing the garbled message problem. This is almost certainly an Entourage problem as if I look at the same messages using Outlook (2007) the messages are fine.

The given workaround is not viable for me as I send emails from a number of different places, including the webmail interface to Exchange. To your knowledge is there a more "workable" fix which actually addresses the issue rather than working around it?

One reader said that this caused by a problem with ActiveSync and Entourage. We've reported two workarounds, here and here. If you've seen this problem

Another take on the iPhone/Exchange garbled messages

Monday, July 13, 2009

Eugene Stakhov is seeing the problem with iPhone messages sent to Exchange showing up as gibberish:

Just joining the chorus, that I'm experiencing the exact same problem here. I haven't tried the workarounds you've listed, and probably won't, as I can use my company's Outlook Web Access to get detailed info on emails I've sent from my iPhone (one of the Microsoft workarounds from KnowledgeBase ). But it definitely is frustrating!

If you've seen this issue

TIP: Use IMAP and another port for iPhone/Exchangegarbled messages

Wednesday, September 30, 2009

Andrew Stuart sent another suggestion to fix the problem of email messages from Exchange Server that are garbled when viewed from an iPhone or iPod Touch. We've previously reported several suggested workarounds. Stuart has another:

I have found a fix that works, I set up my Exchange account in my phone as IMAP instead of Exchange. It works like a charm, but a little tricky to get set up initially. I think the key is changing the outgoing server port to 2525. First it will error when setting up, but if you try without SSL, it'll let you then go to advanced settings and change the server port. IT works fine for now until there's an Entourage fix.

If you've tried this approach

TIP: AppleScript prevents iPhone/Exchange garbled text problem

Monday, January 11, 2010

William Smith wrote an AppleScript (downloadable here) that solves the problem of messages sent from iPhone to Exchange appearing garbled in Entourage. He also posted an explanation at the Microsoft Entourage blog:

While browsing the web I came across your page about the iPhone/Exchange Sent Items problem where messages sent from an iPhone appear as garbled text in Entourage.

I posted an entry about this on The Entourage Help Blog in August 2008 that explains why this happens and under what circumstances. I also posted an AppleScript to allow folks to read these messages and others (in the comments) have taken the script further and automated the process so that users don't need to see this anymore. You'll find my post here: "Use AppleScript to read ActiveSync Sent Items in Entourage"

If you've tried this

TIP: Another AppleScript for garbled Entourage email sent from iPad

Wednesday, March 9, 2011

Jeff Latimer is seeing the problem of email messages from Exchange Server that are garbled when viewed from an iPhone or iPod Touch, except he sees the problem only with iPad-generated mail. He tried an AppleScript we mentioned, but he found another that works better:

I see this issue for any messages sent from my iPad. All other messages sent from either Entourage or my iPhone seem to be OK. It is when I look in my sent folder that I see the messages. They appear to look like they were encrypted, but from what I am reading they seem to be missing some information in the header and that's causing the messages to look strange.

I did try some of the AppleScript workarounds. First I tried the single message version found on the Entourage Help Blog I found on your site. I actually decided to modify the script a bit myself for my own purposes, but it was still a slow process. I had over 500 messages to go through, so I started reading deeper into the thread on the Entourage Help Blog and found another script by user "Levi" (here's the link to the comment he posted). It allows you to select multiple messages and it saves them to your desktop in a folder that is time date stamped and the messages get named in an auto-sequenced order so they don't ever overwrite one another. (This was basically the same thing I started doing with my own version, but this one was more "automatic" than my version was.) Anyway, it worked perfectly. It's by far the best solution I've seen. I now have that script in my arsenal and use it from time to time to clean things up. It would be nice if Microsoft would fix the problem for real, but I guess that's a long lost hope now.

If you've tried this AppleScript

Current news on the MacWindows home page.


TIP: iPad/Exchange garbled email has same fix as iPhone

Thursday, April 22, 2010

Ann Rittenberg reported seeing the same problem with email from Exchange Server on her iPad that we previously reported for iPhones. Email messages from Exchange Server appeared garbled when viewed from an iPhone or iPod Touch--and now, iPad. Fortunately, Rittenberg also discovered that one of our previously reported fixes for iPhone also works on the iPad. She wrote:

Thank you so much for your 10/6/08 post on your site. I had the problem using Mail on my iPad and used the workaround you suggested of moving sent items to a new folder; all the formerly garbled messages displayed perfectly.

My tech support at 123together.com sent me another article, but I haven't activated this suggestion yet because I'm not familiar with all the gory details of code and I got addled by reading the long thread. I think there's something of use here and will try it when I feel stronger!

If you've seen this issue with an iPad

Current news on the MacWindows home page.


Reader reports iPad/Exchange syncing problem

Monday, June 7, 2010

Glen Haubold has a problem syncing an iPad with Exchange Server:

This drives me crazy. I have the new iPad, and our university has Outlook Exchange 2007. Set up was a snap, and everything syncs perfectly - except the little icon that tells me that the message has been replied to or forwarded. The iPad marks them, and of course Exchange marks them - but the icons don't sync. I'm surprised that I can't find that mentioned anywhere

If you've seen this problem

iPad/iPhone Exchange sync problem a known issue

Thursday, July 29, 2010

Katrina Thomas found some information about a problem with iPad and Exchange, where icons for replied and forwarded messages don't sync. Thomas found the problem also occurs with iPhone. She also found some information pointing to a technical problem with the way Apple's software communicates with Exchange:

I have reproduced this problem with the iPhone and Exchange 2003. I had to do some research on this a while back and this is what I found. This is from an article from Windows IT Pro:

'Additionally, Apple isn't using the proper Exchange ActiveSync (EAS) verbs for message replies and forwards. EAS "smart reply" and "smart forward" verbs let applications tell the server to include the relevant message text, and the verbs also update the read/forwarded status so that other clients reflect the actions taken.'

This is definitely a recent known issue that has been reported to Apple (dated Aug 2009, OS 3.0) as described in the Apple Discussion forums, here and here.

This does not mean however that Apple has acknowledged this issue...I have submitted feedback regarding this issue and have tried to speak with Apple support, but have yet to receive a response or an ETR.

This problem is also being experienced with the Palm Pre, according to this article.

I also just received a confirmation that this problem continues to exist if you are using Exchange 2007.

If you've seen this issue

Another report of iPhone/Exchange status icons not syncing

Tuesday, September 14, 2010

Harry Kok has the problem of status icons for replied and forwarded messages not syncing between iPhone and Exchange Server:

This problem indeed is exactly what I see as well, and is quite annoying. I wonder why this has not been resolved. Blackberry, my previous phone did not have this problem.

More iPhone/Exchange status icons not syncing

Monday, November 29, 2010

Mike Page also has the problem of iPhones not syncing status indicators with Exchange Server:

Been searching everywhere for a fix for this and this is the first site I've found with sensible info. I've set up ActiveSync on iPhone, which was quite easy. It worked like a charm but no status icons, which makes me question the worth of the whole thing. If I don't know if I've replied or forwarded a mail, what's the point? It really is time this was fixed.

If you've seen this

Reader says iOS update fixed iPhone/Exchange status icon sync issue

Monday, January 10, 2011

Mike Page updated his previous report about iPhone/Exchange status icons not syncing:

We have status icons! Looks like the last iOS upgrade took care of it.

If the last update helped you with this issue

iOS update, Exchange 2010 both needed for iPhone/Exchange status icon sync issue

Monday, January 24, 2011

Doctor Osos commented on the post "Reader says iOS update fixed iPhone/Exchange status icon sync issue," saying that Exchange is also key to the fix:

Hello, it's a combination of two things for Reply & Forward flags (status icons) to work: Device with iOS 4, and Exchange Server 2010 on the backend.

If you agree (or not)

Reader verifies iOS/Exchange updates fix status icon sync problem

Wednesday, April 27, 2011

Sophal Tea confirmed that updating both iOS and Exchange 2010 fixes the problem of iPhone/Exchange status icons not syncing:

I did not realize this, but this is working now. I never bothered to check since it's always been a problem. Just checked and it is working. Bad for those who have Exchange 2007 or older.

If you've seen this issue

Current news on the MacWindows home page.


Messages deleted in Outlook/Exchange remain on iPad

Monday, August 9, 2010

Nick Atalla is another reader reporting a problem syncing iPad and Exchange Server. He also reports another problem, where messages deleted in Outlook remain on the iPad:

I've run into the same problem that Katrina Thomas reported in your blog. I'm running Outlook 2010 on my laptop and syncing my iPad with my domain Exchange service - Exchange 2010. It appears that once I've opened/replied to an email message on my client, before a sync could take place with my iPad, I never see the message on my iPad. I can't be sure that this is always the case - I'm going to try and follow more closely.

I've also found that when I delete a message in Outlook, the message remains on the iPad. When I try and delete the message on the iPad, I get a message on the iPad that the action could not be completed.

I'm hoping this isn't what happens on my iPhone - I just ordered a new iPhone 4G. Also hope that the issue around sync go away when the iPad is updated with iOS 4. I love the iPad -- but it has to work properly with Exchange.

If you've seen this

TIP: Rebuild .OST to fix Outlook, iPad, Exchange sync problems

Sunday, August 15, 2010

John Lundell said that problems with Outlook and iPads and iPhones, such as where messages deleted in Outlook remain on the iPad, are due to a corrupt Outlook file in Windows:

The user having these issues needs to re-create their .OST file. We've seen similar things (not just with iPads or iPhones) all related to corrupt .ost files.

Microsoft has information on how to fix a .OST file here.

If you've tried this approach

Reader confirms rebuild Outlook .OST file fixes iPhone, Exchange sync problems

Monday, February 14, 2011

Jeffrey Kerber confirmed a previously reported tip that rebuilding a .OST file in Outlook for Windows fixed a problem with messages deleted in Outlook remain on an iPad. However, Kerber uses an iPhone: I tried the tip and it worked! I have an iPhone, but same difference!

If you've tried this

Exchange email deleted with Entourage stays on iPhones

Tuesday, September 7, 2010

Kirk Spencer has the problem where Email deleted with Entourage stays on iPhones. We've had a previous report, and a suggested fix, about the problem occurring with Outlook. Spencer reports:

I finally found someone with my problem. I have found lots of web pages with solutions for syncing problems, but not this specific problem. I had been using 3G iPhone (iOS 4.0.2) and Entourage 2008/ Exchange server on Intel Mac with no problems. Only recently -- the last several weeks -- the iPhone receives new email messages fine, but when you delete in Entourage, the messages stay on iPhone.

I can delete emails on iPhone. I can send new mail from iPhone. I receive new emails on iPhone. Calendar and contacts sync fine.

If you've seen this problem

iPhone 3G and 4 also have problem of email deleted in Entourage not deleting on iPhone

Wednesday, September 29, 2010

Archna Johnson saw both iPhone G3 and iPhone 4 having the problem of email not being deleted on the iPhone after being deleted in Entourage. (The problem has also bee reported on iPads.) Johnson wrote:

I started seeing this problem a couple of weeks ago on my iPhone 3G. I just bought the iPhone 4 and it seems to have the same problem. I do see this as being reported on the site.

If you've seen this problem

TIP: Workaround for mail deleted on Entourage that stays on iPhone

Thursday, October 7, 2010

Archna Johnson follows up on her previous report with a workaround to the problem of email not being deleted on the iPhone after being deleted in Entourage:

I was able to fix the problem by emptying the cache for the folder and restarting Entourage.

Our first report of the problem was for an iPad. If you've tried this workaround with an iPhone or iPad

TIP: Workarounds for iPhone/Exchange problems deleting email, calendar syncing

Friday, October 22, 2010

Ken Stevens found methods of getting around problems with iPhones and Exchange Server. These include deleted emails still remaining on the iPhone and calendar syncing problems:

My wife has had many of the iPhone 4 and Exchange problems that are shown on this site. I believe that we have found a fix/easy work around -- it worked for us and many others so far. We are in Australia and all the phone concerned are on the Telstra network but this fix may work for other networks as well. We have not yet been able to test it on another network.

We first did the update to iOS 4.1 and installed the patch from Apple to extend the server time out period - this did not fix the problems.

Next we deleted the Exchange account and recreated it - this fixed the problem with deleted emails still showing up on the phone and the blank emails but still no calendar sync.

By chance a few days later I left the iPhone connected to our wireless network overnight - amazing the calendar was now synced and all of the other problems were gone. It has now been several weeks and none of the problems have returned.

I believe that the problem occurs with Exchange accounts that already exist and contain a large amount of data. This is preventing the phone from syncing. It must have something to do with the internal setting of the phone exchange or network that cannot be changed on the phone by the user or it could be something strange with the Telstra 3G network.

If you've tried these workarounds

Current news on the MacWindows home page.


Garbled Mail sent from iPad Exchange account linked to European characters

Tuesday, June 15, 2010

Bo Hejl described a problem with sending mail from an iPad's Exchange account. It sounds similar to a previous report about iPad/Exchange email, where a solution was offered by a reader. Hejl reports:

If I compose a mail on my iPad or iPhone, using my exchange account, European characters (æ, ø, å and other accented characters) will be ineligible when the message has been received and is read in another account. It is not quite consistent, however. Mail sent from Exchange to MobileMe is garbled when read on the iPhone and iPad, but not on web-MobileMe, mail received by an imap account tend not to be garbled, but is occasionally.

I have tried to change settings on my Windows Exchange client (character sets, HTML formatting) but to no avail. The problem is significant when mails are forwarded to different type of clients, responded to etc.

If you've seen this

Current news on the MacWindows home page.



iPad/Exchange email message all marked as "read"

Tuesday, June 29, 2010

When viewing his Exchange email from his iPad, Mark McKenna sees all of them marked as "read:"

I'm using an iPad to access my work Exchange account. Setup took about two minutes and seems to work fine except all messages show up as "read" even when my work computer is turned off.

If you've seen this issue

iPad/Entourge problem reported for iPhone4; Exchange emails marked as "read"

Tuesday, July 20, 2010

James Miller sees email from Exchange Server all marked as "read" on his iPhone 4. The problem was previously reported with the iPad. Miller reports:

I am using Gmail on my iphone4 and have it set up per Google's instructions to use the "Exchange Server" option. Sometimes emails in my "all mail" folder show up as read when I know I haven't read them on my iphone4 or my computer. Why is this happening?

If you've seen this problem with an iPad or iPhone

Explanation for Exchange e-mails on iPhone/iPad marked as read

Thursday, July 29, 2010

Luis Antezana has an explanation of why people see all Exchange mail marked as read on iPads and iPhones:

I've seen this happen, too, but the explanation seems pretty straightforward. iPad always has an e-mail selected in its mail app, which is marked as read. If your iPad is set to automatically check for new mail and you're viewing and deleting mail from another location, iPhone/web/etc., then you may have deleted the message that was previously the selected e-mail in iPad. In this case it seems iPad replaces that previously selected e-mail with another one, and marks it as read. This would cause a message to show as read in whatever list you're checking remotely even though you've never viewed it. I haven't tested this to ascertain if iPad does this based on the e-mail's numeric position in the list or some other scheme, but this is my general feeling for why this happens. I'm also 95 percent sure this happens on non-Exchange-based servers.

If this jibes with your experience

Current news on the MacWindows home page.


TIP: DNS fix for iPhone iOS4 error in Exchange inbox

Tuesday, June 29, 2010

Brian Povlsen reports an Exchange problem with the new iOS4 for iPhone that produces an error in an Exchange inbox. The solution (for network administrators) is to use A records instead of CNAMEs in the DNS server:

Some individuals from the Apple Discussions forum said that they are getting the error "Server is unavailable" in their inbox on a Microsoft Exchange 2003 account. These accounts worked normally before the upgrade. Archilies has the solution: "I had the same issue. It appears that the mail client in iOS 4 does not like CNAMEs. I had to change our DNS zone to use A records instead of CNAMEs for our mail server." This is verified by other posters on the thread." The post about this can be found here.

If you've seen this problem

Reader confirms DNS fix for iPhone iOS4 error in Exchange inbox

Tuesday, July 20, 2010

TIP: DNS fix for iPhone iOS4 error in Exchange inbox

David Martin confirmed a tip for fixing the problem with iOS4 for iPhone that produces an error in an Exchange inbox:

This works and is the resolution if you are looking up a local DNS name on a windows network that has .local as the domain extension. I have xxx.local and my exchange system uses the external dns name of office.xxx.com.au when I had a CNAME in the DNS for office.xxx.com.au pointing to the xxx.local the email reader would not connect to the server. I changed the CNAME to an A using the IP address, and presto, the local resolution now works.

DNS fix for iPhone, status icon sync, seen on more iOS versions

Wednesday, September 29, 2010

Sophal Tea confirms the Exchange problem with the iOS for iPhone that produces an error in an Exchange inbox, fixed with a DNS tweak. Tea also sees the problem with status icons not syncing with Exchange:

I have just found out the same problem regarding the DNS and CNAME. I think that's retarded. I found out by downloading a DNS lookup tool on the iPhone and whenever I Query the Exchange Server, it would hang the app and eventually give out an error. I don't believe it's just iOS4, it's been a problem period.

The other problem that I see is the status icon not syncing. That's the same since iOS2 or whatever you want to call it. It hasn't been fixed. That's never addressed. The other component that iPhone is lacking is the Task List. WinMo5 had this support, not sure why Apple decided that we don't need to sync to-do lists.

More on CNAME DNS problem for iOS and Snow Leopard

Wednesday, December 22, 2010

Kevin Parker responded to two reports about DNS problems with CNAME lookups with iPhones ("TIP: DNS fix for iPhone iOS4 error in Exchange inbox") and with Snow Leopard ("Mac OS X 10.6.5 breaks DNS CNAME lookups"). They may be related:

We are experiencing this, but it appears to be a bigger DNS issue with CNAMEs, and in our case, affects Mac OS X 10.6.x, iPhones, and iPads. I added comments to this Apple thread, but also copied them here below:

I am experiencing the same issues re: unable to connect to a server via its CNAME record pointing, a FQDN (server1.ourdomainname.NET), internally to an A record. I can look up the information and see the A record and IP to which this ".net" zone CNAME points, but I can't ping it.

Strangely, we have another CNAME record for "server1.ourdomainname.LOCAL" that points to the CNAME "server1.ourdomainname.NET" (the one I can't reach internally), and THAT one resolves fine. But it doesn't help when it's our mail server and I need to be able to access both on and off site.

THIS IS NOT LIMITED TO MACS. Our iPhones AND iPads are experiencing the exact same behavior. I.E., they can reach the FQDN externally, but not internally. This all happened about the same time. Windows clients are unaffected by this one DNS oddity on our network. Even my Windows 7 VM on my Mac can resolve the FQDN fine internally.

If you've seen this issue

iOS DNS issue with CNAME pointing to .local

Wednesday, February 2, 2011

Tim Fryer responded to previous reports of problems with iOS 4 and DNS CNAME lookups. Unlike some readers, Fryer is not seeing the problems with his Macs:

I am doing some research regarding the possibilities of bringing Mac's and iPads into our Windows domain. The Macs work just fine. Joined to the domain, we loaded MS Office 2011 and Firefox and we are working pretty much the same way as a PC. The iPad's (and iPod's too) however could not resolve DNS correctly. It took some troubleshooting, but we found that any CNAME in our external .org domain that pointed to our internal domain name that ends in .local failed. Everything except iPad's and iPod's work just fine. So there appears to be a bug as you mention in the iOS regarding CNAME and DNS lookups.

If you've seen this problem

TIP: Apple says iOS 4.1 fixes iOS/CNAME DNS problem with .local

Monday, February 14, 2011

Apple tech article TS3389 says that iOS 4 devices are unable to resolve DNS names that end with a .local suffix. The article recommends upgrading to iOS 4.1 or later to fix this issue. Peter Gort alerted us to the Apple article, in response to our reader reports:

On the front of your web page this morning I found a question about iOS DNS issue with CNAME point to .local. This article might be relevant.

The Apple article also recommends not using .local:

Bonjour's Multicast Domain Name Service (mDNS) uses the ".local" suffix to identify Bonjour-accessible devices. When planning for internal corporate network naming, to avoid conflicts with Bonjour, consider using a different domain suffix, such as one of the following: .private, .intranet, .internal, .lan

If upgrading to iOS 4.1 fixes this issue

TIP: Another suggestion for iOS DNS issue with CNAME pointing to .local

Monday, February 14, 2011

Søren Theilgaard got around the iOS/CNAME DNS problem by pointing directly to the host with an A record instead of a CNAME, a suggestion first made last June:

I have implemented Kerio Mail server on a Mac OS X Server in a small Windows environment, where the Mac server was named with a .local domain. The Mail server name was mail.domain.dk and pointed (CNAME) to macserver.domain.local.

The Exchange account on their iPhones worked perfectly when outside of the office, as the mail server name was an A record to their public IP address. Inside in their local office it failed. After I changed the DNS so that it pointed directly to the host, everything worked fine.

If you've tried something similar to this

TIP: Apple says iOS 4.1 fixes iOS/CNAME DNS problem with .local

Monday, February 14, 2011

Apple tech article TS3389 says that iOS 4 devices are unable to resolve DNS names that end with a .local suffix. The article recommends upgrading to iOS 4.1 or later to fix this issue. Peter Gort alerted us to the Apple article, in response to our reader reports:

On the front of your web page this morning I found a question about iOS DNS issue with CNAME point to .local. This article might be relevant.

The Apple article also recommends not using .local:

Bonjour's Multicast Domain Name Service (mDNS) uses the ".local" suffix to identify Bonjour-accessible devices. When planning for internal corporate network naming, to avoid conflicts with Bonjour, consider using a different domain suffix, such as one of the following: .private, .intranet, .internal, .lan

If upgrading to iOS 4.1 fixes this issue

TIP: Another suggestion for iOS DNS issue with CNAME pointing to .local

Monday, February 14, 2011

Søren Theilgaard got around the iOS/CNAME DNS problem by pointing directly to the host with an A record instead of a CNAME, a suggestion first made last June:

I have implemented Kerio Mail server on a Mac OS X Server in a small Windows environment, where the Mac server was named with a .local domain. The Mail server name was mail.domain.dk and pointed (CNAME) to macserver.domain.local.

The Exchange account on their iPhones worked perfectly when outside of the office, as the mail server name was an A record to their public IP address. Inside in their local office it failed. After I changed the DNS so that it pointed directly to the host, everything worked fine.

If you've tried something similar to this

Current news on the MacWindows home page.


TIP: Apple fixes slow iOS 4-to-Exchange syncing, server slowdown

Friday, July 2, 2010

Apple has released a new ActiveSync profile for the iOS 4 operating system for iPhone and iPod Touch. The profile fixes a problem where iOS 4 devices experience slow syncing of mail, contacts, or calendars with Exchange server, or experience no syncing at all. Even worse, Apple said that the problem could cause Exchange Server to slow down.

The new ActiveSync profile increases the amount of time the iOS 4 device waits for Exchange Server to respond to sync requests. The default is 30 seconds, which causes the iOS 4 device to make repeated requests to sync with Exchange Server.

If you've seen this issue and tried Apple's fix

Mixed results for Apple's fix for iOS4 iPhone/Exchange bug

Thursday, July 8, 2010

Apple's new ActiveSync profile for iOS 4 for iPhone and iPod Touch may -- or may not -- fix the slow syncing with Exchange and/or server slowdown. Scott Hutchinson said it doesn't for him:

Sadly, this fix does not work and iOS4 has totally bricked my 3G as far as work email goes.

Jacob Pyle had better luck:

I had this issue with an Exchange 2007 server. The new profile seems to have fixed it. I hope it's included by default in an upcoming iOS4 release.

If you've seen tried Apple's fix


Current news on the MacWindows home page.


Keeping Exchange email on iPad

Friday, July 2, 2010

In our iPhone and Exchange forum, Craig asks:

Does anyone know how to stop deletion of email on the iPad when it is deleted from the exchange server? I want to be able to keep the emails on the iPad even when it is deleted off the exchange server.

If you know the answer, post a reply to his message here in our forum.

Keeping Exchange email on iPad: use POP3

Tuesday, July 6, 2010

A reader in our forums answered the question how to stop deletion of email on the iPad when it is deleted from the Exchange Server. He suggests setting up the account as POP3.

Current news on the MacWindows home page.


Reader's iPhone/Exchange duplicates email sevenfold

Monday, August 9, 2010

Brian Beck reports an annoying problem with duplicate email sent from iPhones through Exchange Server:

If my boss responds to or sends out an email to anyone at our company, they get several copies of the same email. Every time he sends an email from his phone, 7 copies of the same message are sent to the same person over an hour's time.

If you've seen this

Duplicate iPhone/Exchange email also seen with iPad

Thursday, October 7, 2010

Leonard Chesongol is also experience the problem described in Reader's iPhone/Exchange duplicates email sevenfold. Except that Chesongol is seeing the problem with iPads:

I found your post regarding Exchange duplicate emails. I'm experiencing a similar issue with my iPad users and was wondering if you had a solution to this annoying issue?

Elsa Gonzales has the problem in the iPhone 4:

Regarding the problem of an iPhone 4.0 (which works with Exchange) sending multiple emails (of the same message). One of our associates has recently experienced this situation (on 9/27/2010) while he was at the AirPort. He sent the email out to his secretary and a couple other associates and it was delivered 5 times to each recipient. It hasn't reoccurred.

If you've seen this problem

Another report of duplicate email iPhone/iPad/Exchange email

Wednesday, November 24, 2010

Mike Cottingham is seeing duplicate email sent from an iPad, and thinks it's the sync:

Our President's iPad recently started seeing the types of issues mention here. Emails are sending multiple times, the sync times seem to be very long or do not occur at all. It's like the iPad is restarting the sync process several times.

If you know of a workaround

Current news on the MacWindows home page.

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Reader's iPhone email not getting delivered through Exchange

Monday, August 9, 2010

James Linck's email doesn't get delivered through Exchange:

You said if you've tried Apple's fix for the Exchange email problems on the iPhone and it didn't work, let you know. Well, I did and it doesn't work. Very often (although I have no idea when or why it will occur) my e-mail simply stops getting delivered. It doesn't stay in my outbox, go to sent mail or any other folder and never gets to the recipient. You can imagine the problems this causes. I won't notice it, will have replied to many people, then I'll realize that e-mail isn't working. I cannot recall which emails I sent and they are gone!

If you've seen this problem

Another reader can't send iPhone/Exchange mail after iOS4

Monday, August 30, 2010

After upgrading to iOS4, Michel Wijnstekers is having the same problem described in the report "Reader's iPhone email not getting delivered through Exchange." He says:

I have the same problem as described in the website. We updated our e-mail server (new install) to Exchange 2010. Everything was working fine. But when iPhone users updated their IPhone to version 4, they were unable to send mail from their iPhone. There's no error message on the iPhone and the mail is not in the sent folder. Also, some of the users must fill in their password on there iPhone several times in a week.

We using Exchange 2010 and Microsoft UAG to publish Exchange to the web.

If you're seeing this issue

Reader says iOS 4.1 fixed problem with undelivered mail

Monday, September 20, 2010

Michel Wijnstekers updated his previous report about upgrading to iOS 4 causing iPhone email to not get delivered through Exchange. He said the iOS 4.1 update fixed it:

Regarding iPhone email not getting delivered through Exchange. The Problem is resolved after the last iPhone update. Everything works fine now.

If you've seen had the problem and updated to iOS 4.1


iOS4 breaks Exchange mail for some readers; ActiveSync update didn't help

Sunday, August 15, 2010

Readers are reporting Exchange email problems after upgrading iPhones and iPod Touches to iOS4. We've previously reported Apple's release of a new ActiveSync profile, but that doesn't help some readers. David Kerwin saw multiple problems on his iPod Touch with iOS4:

The moment I downloaded iOS4 I knew I'd made a mistake (iPod Touch 3G purchased 12-09). The battery doesn't last more than a day with normal use whereas before it would last a few days. My work email (Outlook 2003) instantly stopped functioning and I've tried every fix except jailbreaking and reverting to iOS 3.1.3, which I've heard can cause problems. It is really annoying. I've been telling everyone I know not to download the new operating system.

Dorwin Birt said the Apple ActiveSync upgrade didn't help:

One of my clients has an iPhone 3G. Since he upgraded to iOS4 he has had the Exchange Sync problem. Can't sync at all. The Apple ActiveSync profile did not help at all.

Joe Hedrick can't access Exchange mail after upgrading to iOS4:

I have given up trying to retrieve my work e-mail (via Exchange). Gmail is no problem. Did Apple not test such a basic function? I am running on a 16GB 3G and have also experienced all the other reported performance issues. [iOS4] is the worst Apple product in a loooong time.

If you've seen these problems with iOS4

Current news on the MacWindows home page.


Upgrade to Exchange 2010 stopped iPhone from receiving email

Wednesday, September 29, 2010

Since updating Exchange Server 2010, Alan Oh can no longer receive email on his iPhone:

We just upgrade to Exchange 2010 and iPhone stopped receiving emails. I just upgraded the iPhone IOS to 4.1 but the problem was still there.

If you've seen this problem

TIP: Microsoft fixes for iPhone not receiving mail from Exchange 2010

Thursday, October 14, 2010

Magnus Björk in Sweden sent us two links to Microsoft pages describing possible fixes for problems with iPhone receiving email from Exchange Server 2010. Björk reports:

I think you might have hit the redirect issue with iPhone and Exchange 2010. When an iPhone connects to the new Exchange 2010 CAS (Client Access Server) and the mailbox is still on Exchange 200x (coexistence) the users gets redirected to the CAS (or Front-End) of Exchange 200x. It seems like iPhone doesn't honor the URL sent back and therefore doesn't work. How this is done in Exchange is described at this Microsoft blog. A way to fix it is to move the mailbox to Exchange 2010 or change the URL in the iPhone to the legacy URL.

A second suggestion: If the first solution I sent you doesn't work you might have a problem described here. Scroll down to "7. iPhone, OWA Premium and POP3 & IMAP4 issues due to invalid accepted domain." The given resolution is to run the a command under Exchange Management Shell.

If you tried either of these two approaches

TIP: Workaround for iPhone not receiving email from Exchange 2010

Friday, October 22, 2010

Kym Blackwell sent us a workaround for a problem where iPhones stop receiving email after upgrading to Exchange Server 2010:

I had the very same thing last week when we migrated from Exchange 2003 to Exchange 2010. What I did to resolve was go to the Active Directory Users & Computers, under each user that has a iPhone problem "Properties" > Security > tick the inherit permissions" box. If it is already checked then try unchecking it, Apply then check it again. After that, you need to delete the Exchange for Mail account profile from the IPhone and recreate.

If you've tried this fix

Reader success with fix for iPhone not getting email from Exchange 2010

Wednesday, November 24, 2010

Amanda Hartman confirmed a suggestion for fixing an iPhone problem of not receiving mail from Exchange 2010. The suggestion recommends "to move the mailbox to Exchange 2010 or change the URL in the iPhone to the legacy URL." Hartman did the later:

I just changed the URL to point to the legacy server and it worked like a charm! Thanks so much!

If you've seen this work

Related: iPhone Tips and Reports

Current news on the MacWindows home page.


Exchange appointments not appearing in the iPhone calendar

Thursday, October 7, 2010

Steven Cross reported a problem where Exchange appointments are not synching with an iPhone:

I have seen a problem that appointments sent to me and accepted do no get synched to the iPhone calendar. They do show in OWA and in Entourage/Outlook. I have not found a workaround. I did try the Apple profile update mentioned. It did not work. I am using iOS 4.1.

If you've seen this problem

Suggestion and more reports for iPhone/Exchange calendar problems

Thursday, October 14, 2010

A number of readers responded to the report Exchange appointments not appearing in the iPhone calendar with reports of this and similar problems. Jim Dwyer sent a suggestion:

My Exchange account has created a separate calendar related to that e-mail address which appears at the bottom of my (much too long) calendar list on iPhone. It could be that others have failed to find and activate this account so that it will appear with any other calendars they have checked for inclusion in the calendar display.

If this helps you

Steven Cross, who first reported the problem, sent an update:

I did have some appointments come through at random the other day, don't really know why, I still have 10 percent missing, they may come through, I am watching. It was very obvious and random. The notifications were a month old.

Jen Oates has performance problems:

I have an iPhone 4.0.2. My mail and calendar are either slow or simply don't sync with our university's Exchange server. Outgoing mails aren't always being sent either.

Lane is using Outlook for Windows, not Entourage, but also sees the problem, but randomly:

I too have seen this behavior (iPhone 4.1, Exchange 2007 sp2, Outlook 2010). It appears to happen at random and does not affect all meetings only a select few. If I compare Outlook and OWA all meetings show in sync correctly however the iPhone will be missing a few meetings here or there. If I blow away the email config on my iPhone and then reconfigure and sync with Exchange, the missing meetings still do not appear on the iPhone but they do show in OWA and Outlook. I've tried comparing the missing meetings with known good meetings that sync correctly within MFCMAPI but I can't find anything that would indicate why it will not sync to the iPhone correctly. One thing that was interesting in testing was if I configured a Windows Mobile device to connect to Exchange the problem meetings synced correctly to the device.

TIP: Workarounds for iPhone/Exchange problems deleting email, calendar syncing

Friday, October 22, 2010

Ken Stevens found methods of getting around problems with iPhones and Exchange Server. These include deleted emails still remaining on the iPhone and calendar syncing problems. To read his report, click here.

TIP: Workaround for Exchange/iPhone calendar sync problem

Monday, March 5, 2012

Irit Rosdeutscher sent us a workaround for the problem of Exchange appointments not appearing in the iPhone calendar:

I have iPhone 4 version 4.3.1 connected to an Exchange account. The calendar on Exchange is only partly synced. I can't determine why some appointments are synced and others are not. To fix it, I did the following:

  1. I turned the Calendars in this account OFF (deleting all entries).
  2. I turned it back ON.

This caused the calendar to re-sync and now it works fine (at least so far), i.e. any new/deleted/updated appointments are getting synced instantly.

If you've tried this suggestion

Exchange appointments not appearing in the iPhone calendar

Friday, December 17, 2010

Gareth Weston has the same problem as decribed in "Exchange appointments not appearing in the iPhone calendar:"

Having the same problem as described by others on an iPhone 4 also on my old iPhone 3G. I have Entourage with Exchange Server. About 20 percent of calendar entries do not sync. WebMail and Entourage show correctly. No pattern on the missing items.

More reports of iPhone/Exchange calendar problems

Monday, January 3, 2011

Two more readers report problems with Exchange appointments not appearing in iPhone calendars. Edward Gonzalez sees this throughout his company:

In the company I work for, we're experiencing the same issue. The Outlook profile update doesn't seem to work most of the time (although seems to work at first, but quits working after a couple of days). I've worked with MS support on this, and they can't pinpoint the issue either. It's only affecting my iPhone user base though.

Like another reader P.J. Farmer sees the problem randomly. Our posted suggestion didn't help:

I too have random problems with calendar syncing with iPhone 4, iOS 4.1, Active Sync with Exchange 2003. Most appointments appear, but not all. Most of the disappearances seem random, except one exception - if someone cancel/deletes one meeting out of a reoccurring meeting, then none of the occurrences of that meeting will show again.

Thanks for this suggestion. Unfortunately it did not have any impact.

I also have an iPad that sits at home on wireless all day long and has the same problem with Calendar syncing. I deleted the Exchange calendar from my iPad a month ago, and now there is only my iPhone attempting to sync. But nevertheless, no improvements.

Reproducing problem of Exchange appointments not appearing in iPhone

Tuesday, January 18, 2011

Josh Thompson found the sequence of events that reproduces the problem of Exchange appointments not appearing in the iPhone calendar:

I have seen this problem as well. We have narrowed it down to a reproducible test case.

  1. Send a meeting invitation.
  2. Accept in Outlook.
  3. Update the meeting invitation (change the time or something).
  4. You cannot accept the new invitation on the iPhone ("Your response to the invitation cannot be sent" error) and if you accept in Outlook it will disappear from the iPhone but still appear in Outlook.

What is strange is that any subsequent meeting updates will work fine; it only seems to be a problem with the first update.

If you know of a workaround to this issue

Current news on the MacWindows home page.


iPhone/iPad updates don't work for Windows non-admins

Monday, November 29, 2010

Doug Starkey says updates for iPhones and iPads are forcing him to give PC users administrator privileges:

I generally do not let my users have admin level privileges on their PC's. But as time has gone by, I have more and more users with iPhones and iPads. They want to do their updates but find that they cannot because they are not "administrator-level" users. The only solution I have found is to make them a "local" administrator on their PD; but this is only preventing them from trashing my servers. They can still make a mess of their machine just by surfing the web.

I have searched for some method of allowing non-admins to update Apple software on a PC but I'm finding nothing. I'm hoping someone in the MacWindows community has some experience with this and, possibly, a solution.

If you've seen this issue

TIP: suggestion for iOS updates and Windows users

Friday, December 10, 2010

Chris Denesha has an idea about what to do about the issue where iPhone/iPad updates only work where Windows users have admin privileges:

I do not have the solution but can perhaps point the way to one here. The idea is to use FileMon and RegMon to determine what is being accessed by the update process, and selectively applying permissions accordingly.

If you've tried this approach

TIP: An approach for iOS updates for Windows non-admins

Friday, December 17, 2010

Doug McIntyre responded to our report "iPhone/iPad updates don't work for Windows non-admins," where updates for the devices forced an administrator to give PC users administrator privileges: McIntyre talks about Windows permissions and how to use Windows tools to get around this:

I don't have specific experience with these specific programs, but do have quite a bit of experience for other Windows programs. I too am an IT admin that doesn't permit windows users to have any admin privileges on their workstations.

Generally, there are two areas of permissions that need to be relaxed for these classes of applications that are developed with the silly assumption that every user is an admin user. (A problem with letting developers be the admins in a software company I think, but that's besides the issue). Those are the file system privileges, and the registry tree privileges.

To find out which, first get the Windows Sysinternals suite.

You'll really want Process Monitor out of the suite, although the rest can come in quite useful. Run up the problematic application under it and see if you can capture the permission errors for the disk path or registry path for what the application is trying to do.

Unfortunately, I think Windows low-level processing of the registry is a total mess. You'll easily see 1,000's of junk scrolling by as it tries over and over again, or accesses entries that don't exist normally and the apps just move on. Same thing with the disk access, although usually you can guess a bit easier of what it wants to access there.

So, this process unfortunately takes a lot more time and effort than it should. But after a while, you get a sense for which areas of the file system tree and registry tree that things *should* have proper permissions for and don't and fail on. There's also a lot of trial and error, opening up the ACLs on objects in question, and trying again and again.

After you find the problematic areas, open up specific holes for permissions on the registry tree and file system tree with the proper windows tools (ie. basic ones are Regedit and Windows Explorer). Once I find the magic correct combinations, I'd usually make a batch file script to document what I found using command line tools to open up the ACLs on these objects, and can apply it again later at any given date. Or if things change, I have documentation of a starting point of what I did before.

If you tried this approach

Current news on the MacWindows home page.


Reader's iPad Safari disappears when Exchange email set up

Monday, January 3, 2011

Steve Ragas reports a strange problem with Exchange mail on an iPad:

When I set up the Exchange email, Safari disappears. I go to Settings and I can see it there, but it can't be selected. As soon as I delete the Exchange account, Safari returns.

If you've seen this problem

TIP: suggestions for Safari disappearing from iPad with Exchange set up

Friday, January 14, 2011

Two readers sent us a fix for the problem report "Reader's iPad Safari disappears when Exchange email set up." It involves making sure web browsing is not disabled on the server. "Doctor Osos" describes it:

Check the Exchange ActiveSync (EAS) policy. "Enable web browser" is unchecked, causing Safari to disappear from Springboard. (Same can be done with camera from EAS.) I'd stake a chili cheese dog on that. The setting is on the Exchange ActiveSync server (Exchange 2003 - front end or exchange CAS in 2007/2010).

Michael Perbix suggests an Exchange setting:

I believe this is a feature of security profile in E MobileMeBackupv3.2.dmg xchange when setting up profiles for remote devices.. You can disable web browsing, camera use etc etc. The Exchange administrator should be able to fix that, should it actually not be the result of something being done on purpose for security/policy reasons.

If you've tried either of these approaches

Current news on the MacWindows home page.


TIP: Fixing problems with iOS 5 S/MIME signing and Exchange

Tuesday, January 10, 2012

A new Apple new tech article describes a new feature in iOS 5, using S/MIME (Secure/Multipurpose Internet Mail Extensions) with Exchange 2010 for public key encryption and signing of MIME data. The article describes how do deal with three problems with iPhones, iPads, and iPod Touch and S/MIME Exchange mail:

  • Signed and encrypted messages sent from Outlook 2010 to iOS 5 do not appear signed
  • Signed and encrypted message replies and forwards sent by iOS 5 do not appear signed and encrypted
  • Signed messages sent by iOS 5 do not appear signed

If you've tried some of these procedures

Current news on the MacWindows home page.


iOS 5.1 update stops reader's incoming Exchange email

Monday, March 19, 2012

Phil Berg reports that since updating his iPhone to iOS 5.1 he has problems getting email from Exchange Server:

Since 4 of us at our office updated our iPhone 4 and 4S to iOS 5.1, we're all having problems receiving IMAP email from Exchange Server. Some emails are okay, but some we never get. It seems to be random. I can access the messages in Outlook on my PC. We haven't changed Exchange, only the iPhones were updated.

If you've seen this problem

Current news on the MacWindows home page.


Reader reports email not downloading to iOS from Exchange 2010

Monday, April 2, 2012

A reader in our forums reports a problem where iOS devices are not downloading email message to iOS devices, and the devices can't send email. The reader also found an article about it at Microsoft called "iPhone, OWA Premium and POP3 & IMAP4 issues due to invalid accepted domain," which describes a text command to run in the Exchange Management Shell. Here's part of the post:

...We recently upgraded our small office server to Small Business Server 2011 with Exchange 2010. When we did that we became our Mail Server for our company (5-10 employees). We have had no issues with Outlook or Remote Web Outlook or even in setting up and configuring Exchange Email Accounts with iPads and iPhones, all the settings come up verified and it downloads emails in the preview panel. But when you open an email it comes up with "This Message has not been downloaded from the Server". It also doesn't allow you to send emails...

If you've seen this problem or tried Microsoft's fix post a reply in the forum or


Apple discloses iOS bug with Exchange Server; MS advises to block iPhones

Apple has posted a warning of a bug in iOS 6.1 that causes "excessive communication" with Exchange Server, so much that the server could block the iPhone, iPad, or iPod touch from accessing it. The problem can also degrade server performance. Apple described how to avoid the problem and promises a…


Exchange message read on iPhone is only partially visible on desktop

Amanda Schafer reports an iPhone and Exchange problem that affects viewing of messages on a PC:

Exchange seems to be downloading messages just fine to my iPhone, but if I try to view the same messages later on my desktop, only a small portion of each message is visible. The reverse is not a problem. If I open messages on my desktop first, they are still fully visible on my iPhone later.

If you've seen this problem

Current news on the MacWindows home page.

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