Outlook no longer syncs after 2.2 upgrade (USB via iTunes)

Question

Outlook no longer syncs after 2.2 upgrade (USB via iTunes)

After upgrading my 3g iPhone to 2.2 (and upgrading iTunes), calendar sync takes a very long time and doesn't actually update Outlook 2003 sp3. No events created on the iPhone get synced to outlook and vice versa.

Outlook is connected to an Exchange server. I know this is an issue with MobileMe, but it wasn't a problem with USB syncing in the past. This is acting like syncing with MobileMe did before apple changed the MobileMe control panel to not even try to sync when Outlook is connected to Exchange. I hope USB syncing isn't going away as well.

I've tried deleting and reinstalling iTunes (and apple mobile device), rebooting Windows XP sp3, resetting sync history, and rebooting the iPhone.

This worked prior to the 2.2/itunes upgrade (8.0.2).

Also, OutlookSyncClient crashes fairly regularly (even other time I sync the iPhone), though this happened with 2.1 and itunes (8.0). When it didn't crash (in the past - i.e. 2.1), events did sync.

Has anyone solved this issue?

iphone 3g, Windows XP, Outlook 2003sp3, iphone 2.2

Posted on Dec 1, 2008 8:48 AM

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Answer 1

Dec 1, 2008 8:59 AM in response to detroitsongbird

I'm having the same issues with my first gen iphone. Tried all the same things as you, but it syncs the music, then seems to freeze. wont sync mail or pics, etc.

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Answer 2

Dec 4, 2008 5:59 AM in response to Sportrider12584

Update:

I've tried rolling the iphone firmware back to 2.1. That didn't change a thing. Calendar events still don't sync. OutlookSyncClient still crashes.

I've also tried running scanpst.exe and the .ost and .pst file - there were some issues it claimed to fix in the .ost file. I've create a new .pst for personal folders (my original was from outlook 2000, so it didn't support unicode). I've removed offline support from Outlook, deleted all "tasks" (since they don't sync and I've migrated to using ToDo with ToodleDo for tasks).

The only other tip I've seen that caused OutlookSyncClient to crash in early 2007 was repeating tasks. One user claimed that by adding end dates that fixed his issue (haven't tried adding end dates yet), another claimed that repeating tasks that start prior to the calendar sync window caused an issue. These were both with earlier versions of iTunes (7.6) and the iphone os. So, it would truly be sad if Apple has a regression issue here. But, ya' never know...

I have tried reducing the sync window to 1 day prior, and I've tried unchecking it (to allow all past events to sync). No difference.

Here's the odd thing. After reverting the firmware to 2.1 and syncing, all of my calendar events that were previously on the phone, and were not appearing in outlook, still appeared on phone. How can this be? Where is OutlookSyncClient caching the calendar events?

I also temporarily tried neuvasync. However, I can't have all of my calendars mashed into one. If they would solve that issue I've skip outlook altogether. (actually, I'd use gSync to pull from google calendar into outlook, but use neuvasync to sync google calendar with the iphone).

Sigh...

I've since reinstalled iphone 2.2 and have been going though the pain of resetting all of my apps (username passwords, etc).

I believe the problem is OutlookSyncClient, not the iphone OS.

Now, where can I find the previous version of iTunes?

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Answer 3

Dec 7, 2008 5:44 AM in response to detroitsongbird

The next thing I've tried is deleting reoccurring events and recreating them. Most of these events had been split at some point in the past (i.e. usually it's wednesday at 7 pm, but for one week it was changed to another time).

That didn't seem to fix it.

Then I tried (again) uninstalling and reinstalling iTunes. This time I DIDN'T follow the instructions found on the support site for Outlook not syncing. This time I restarted win xp sp3 after uninstalling each item.

-> uninstall itunes; restart
-> uninstall apple mobile device support; restart
-> uninstall bonjeur (on a whim); restart
-> uninstall bonjeur again (it was listed twice - at two different sizes); restart
-> install iTunes; didn't restart; sync; it worked.

Why?

Did the instructions to not restart after uninstalling itunes before uninstalling apple mobile device support cause some component of itunes (outlooksync) to not get uninstalled?

Was bonjeur the problem?

Odd. At least it synced once, though it took a really long time.

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Answer 4

Dec 9, 2008 6:06 AM in response to detroitsongbird

Well, it worked for a couple of days, but now OutlookSync is crashing again and Outlook is not syncing with the iphone. bummer.

Message was edited by: detroitsongbird

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Answer 5

Nestofc

Level 1

9 points

Dec 18, 2008 11:46 AM in response to detroitsongbird

My experience is that the potential actual issue(s) that cause this are still a mystery. There have been several causes found - repeating appointments, corrupt or old pst/ost files, interference from add-ins. I'm not sure what one of these caused my issues, but I still have this issue. A month or so ago I posted this:
http://discussions.apple.com/message.jspa?messageID=8414946#8414946

To summarize I did this:
* Copied calendar to a newly created PST file
* Deleted all calendar entries in my main calendar
* Sync to iPhone: worked
* Copied all meeting invites (from the copy in the newly created PST file) sent to me
* Sync to iPhone: worked
* Copied all meeting invites I sent to others
* Sync to iPhone: worked
* Copied all other meetings by category
* Sync to iPhone: failed
* Deleted each category one at a time and sync'd each time, sync to iPhone worked after one of these.
* Copied all other categories, except one that I suspected, back to calendar
* Sync to iPhone: worked
* Manually reentered all appointments from failed category
* Sync to iPhone: worked

I didn't need to restart Outlook or iTunes in between any of the steps. I did empty the Outlook trash and select send/receive Outlook in between each step to make sure the ost was always up to date with the changes I was making.

The problem still crops up once in a while. Once it does, sometimes I'll get the outlooksynclient crash and sometimes I won't, but the result is the same - no appointments sync either way. My theory is that when this problem reappears, it is a newly created appointment that causes the crash - so far that has always been the case. Sometimes the appointment was entered on my phone, sometimes via Outlook.

What I try to do now is when I enter new appointments, synch soon after. I check to make sure that the sync works, then categorize the appointments. That way, when the crash occurs, I usually have just a dozen or so appointments to sort through. I move all the uncategorized appointments to a temporary pst file - not an ost folder, empty the trash, then select send/receive in Outlook to make sure the ost is up to date. SO FAR, this has always led to a successfully sync - except once.

Then, you can add back each appointment individually, empty the trash, then select send/receive in Outlook, resync, and you will usually find the offending appointment once the outlooksyncclient crashes. Delete that appointment, empty the trash, then select send/receive in Outlook - hopefully the sync will work again. Enter your deleted appointment as a new one.

The one time this method didn't work, I watched iTunes during the sync. It looked like the crash happened when it was syncing contacts, so I played a hunch and deleted a new contact I had recently entered. Emptied the trash, then select send/receive in Outlook and the sync worked. Entered the deleted contact, empty the trash, then select send/receive in Outlook and is was all good again.

Good luck

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Answer 6

Jason L

Community Specialist

Dec 18, 2008 5:12 PM in response to Nestofc

Hi,

Try the general tips in this article: http://support.apple.com/kb/HT1692

Make sure iTunes, the iPhone, Outloomk and the PC are all updated.
Do you see the issue in another user account?
Do you see the issue after Disabling third-party Outlook add-ins?

-Jason

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