Apple iPhone/iPad Issue with Exchange 2003

We are having an issue with several of our Apple devices at the moment when synchronising email from an Exchange 2003 server.

Everything has been working fine for several years and then suddenly on Tuesday afternoon at 14:30 6 of the 35 devices we have stopped working.  All the others work.  This seems to be account related as we can setup one of the accounts not working on a working handset and that handset stops working.

No new mail is collected and it says that it can't connect to the exchange server.  If you delete the account and setup it up again on the phone all the ticks appear and it synchronises all email up to the time it failed and then falls over.

If we set the handset up to pick up only 1 day on the mail setup it works perfectly but we need to be able to setup for longer than 1 days worth of email.

The phones are on version 8.3.

All other users are setup to pick up a month of email and they work fine, these 6 handsets will not connect to the server to collect new email unless they are set to 1 day.

Has anyone ever experienced this?  Nothing has changed on our server at all.
Rich WilkinsAsked:
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Andy MIT Systems ManagerCommented:
Have the ipads/iphones been updated recently? Could be a recent update to their OS causing compatibility issues with the old version of Exchange.

I would check the server - look for any events that indicate a failure. Activesync logs can also be quite helpful.

Are you able to try anything else for connection (android phone, windows phone) - do these work fine with the same details? Do any of the apple devices run an older version of the iOS, do these work fine? Have you checked Exchange connectivity analyzer to ensure activesync working fine on that end?
MB ShaikhCommented:

It is most probably an update issue either at the client side or server side, so please verify if there is any changes took place prior to the issue took place.

Rich WilkinsAuthor Commented:
One of the 6 handsets hadn't been updated for a while, an update on that one didn't fix the problem though unfortunately.

On one of the handsets we have installed a third party app and that works fine, the native IOS mail app just doesn't update unless set to 1 day.

I've looked in C:\Windows\System32\LogFiles\W3SVC1  for ActiveSync logs but there is nothing in there at all (no files).
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Rich WilkinsAuthor Commented:
On the handset end there have been no updates, no server updates have take place at all.  As mentioned in the original post, my user account will work on any handset but these failing users won't work on any handset which says to me it's an account problem.  However, if you run a third party app on one of the failing handsets it works fine, which points towards an issue with the mail app.
Rich WilkinsAuthor Commented:
Found this in the http log...

2015-06-08 10:35:27 17279 80 HTTP/1.1 POST /Microsoft-Server-ActiveSync?User=jbailey&DeviceId=ApplDMPHPUTUDJ8T&DeviceType=iPad&Cmd=Ping - 1 Timer_MinBytesPerSecond ExchangeApplicationPool

jbailey is one of the users who isn't updating.
How big is the user mailbox?  Hopefully not bigger than 2GB, Is the Exchange server 2003 up to date? on Svc packs  and windows updates?  How about the over all mailstore?  not getting close to the max allowed for Exchange 2003?
Rich WilkinsAuthor Commented:
The users mailbox is currently sat at around 500mb so that should be fine.  The server is fully up to date on both Windows and Exchange.

The database is currently at about 65gb, I believe the limit it 75gb.

Getting a lot of these kind of messages in the Event Viewer, although many of them are saying usernames who aren't expereincing the problem so might be a red herring....

The average of the most recent [200] heartbeat intervals used by clients is less than or equal to [480].  Make sure that your firewall configuration is set to work correctly with Exchange ActiveSync and direct push technology. Specifically, make sure that your firewall is configured so that requests to Exchange ActiveSync do not expire before they have the opportunity to be processed.  For more information about how to configure firewall settings when using Exchange ActiveSync, see Microsoft Knowledge Base article 905013, "Enterprise Firewall Configuration for Exchange ActiveSync Direct Push Technology" (

Could it be a timeout thing?  Seems odd to me that it works if you set it to download 1 day but fails if you set it to 3 days or above.
Rich WilkinsAuthor Commented:
Managed to get to the bottom of it!

A user had sent an email to 5-6 of our sales force using one of the new Apple Emoticon's and ExXchange had been unable to process it.  Deleted those emails and the phones and iPads are back up and running perfectly!

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Rich WilkinsAuthor Commented:
Found the solution and posted.
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