Outlook Calendar Item Does not Sync with iPhone/iPad2

Posted on 2014-04-03
1 Endorsement
Last Modified: 2014-04-28
Ok,  I've been working this one for a while...  I have a user with an iPhone and iPad setup to sync mail, calendar and contacts from our Exchange 03 server.  An meeting is created in Outlook and it sync's with the two devices.  Later, there's a change to the meeting date/time/location.  The changes are made in Outlook and show up on the Outlook calendar (and OWA) but the new changes do not sync with the iPhone or iPad...they still show at the original time.  So far it seems limited to this one user.

-Soft and Hard Reset of the iPhone and iPad.
-Made sure both devices are running current iOS version.
-Deleted and forced OST file to recreate.
-Set user to NOT use Cached Exchange mode.
-Cleared out delegates and added them back.
-Made sure Exchange 03 is running current SP's and updates.
-Deleted user mailbox after exporting maibox items.
-Created new mailbox and associated with user then imported old mailbox items.

This happened, seemingly to random events.  Some events have invitees and others do not.  Events are created primarily by his Exec. Assistant who is a delagate with Editor privilages to his Calendar and Inbox.
Question by:sasolo
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Expert Comment

by:Alan Hardisty
ID: 39976607
Does everything else work happily and is the problem isolated to just a single user?

Did the problem occur after updating the iOS version on the iPhone or the iPad?

Do you have a single Exchange 2003 server or do you have a front-end / back-end config?


Author Comment

ID: 39976659
Everything else for this user seems to be working.  Nothing out of the ordinary reported for emails or contacts, and no other user has reported a similar problem.

This issue was first reported while the phone and iPad were running older rev's of iOS, and it seems to have continued even after an upate to the devices since the start of 2014.  I have been able to setup an additional iPad to sync with this user's account and recreate the error on it.  This is what caused me to delete the existing mailbox and create a new one March 1st.  Today is the first day since this change that any problems have been reported.

Yes, i only have a single Exchange 03 server (single exchange server in the domain).  I do not run a front-end / back-end configuration.
LVL 76

Expert Comment

by:Alan Hardisty
ID: 39976665
How many items does the user have in their calendar and other folders within the mailbox?

Is it a large mailbox?

Are you planning to move away from Exchange 2003 soon?

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Author Comment

ID: 39976685
The user is a heavy email user.  We have him set to AutoArchive to keep his mailbox under control, but he can sometimes have a mailbox that over 500MB-600MB before an archive session takes it down.

Right now he's got a 414MB mailbox with 9,176 items.

Yes, we're moving to 2010 and then to 2013.  I've got a server that's being prepared for Exchange 2010.
LVL 76

Expert Comment

by:Alan Hardisty
ID: 39976730
Okay - doesn't sound too huge.

I think the option left is to nuke the actual AD account and mailbox and start afresh with a new one.  That will cause some fun with internal users who will have the old account cached in Outlook, so there will be some tidying up of the NickName files locally for each user but if it's just one user and with everything else you have done, I don't think you have many other options left.

Have you run the activesync test for this user on


Author Comment

ID: 39976769
Yup, we've run the test on the account before and it told us the test completed successfully.  I just ran it again and it passed again.

Would you recommend I try running the ISINTEG util to check and fix problem with the store before deleting/recreating his AD and EXchange accounts?

...and it will be fun for those that have his old account cached.
LVL 76

Accepted Solution

Alan Hardisty earned 500 total points
ID: 39976787
As you've already exported, deleted and then re-created the mailbox, I'm not convinced that isinteg would do that much, but it's rude not to try first.  Destroying the entire AD account is quite severe, so if the whole store isn't huge, then it may well be worth dismounting and integrity checking it before blowing the AD account away.

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