Calendar Not Syncing - Windows XP and Outlook

I was having the same problem with my calendar AND contacts syncing but after going thru iTunes' Edit\Preferences\Devices and then selecting "Reset Sync History", I was able to sync without any problems.

Hope that helps.

Just something that worked for me...

Using Outlook 2003 with Exchange, iTunes 8.0.1.11
Had dreaded outlooksyncclient.exe crash for weeks. Finally sucked it up and 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

It was a PITA, but it worked. Was syncing fine for 3 weeks until it failed again two days ago. Instead of going through all the same, I played a hunch and viewed all my recurring appointments (Outlook menu view/arrange by/current view/recurring appointments). In this view, I noticed that one appointment had a blank Recurrence Pattern, Recurrence Range Start and Recurrence Range End. This was a recurring appointment I had originally entered on my iPhone. I deleted this appoint, did a sync - everything good again.

Note that I didn't need to restart Outlook or iTunes in between any of the steps, including the most recent appointment deleted and synch.

Thanks Nestofc! It worked for me.

Config: windows xp pro sp2 with Outlook 2003.
Outlooksyncclient.exe crash for last 2 weeks. Been working since 2007 when I got the phone.

1. Export entire calendar folder to newly created PST file
2. Delete all calendar entries (leave the entries in the archive folder if there is any)
3. Sync to iPhone: Failed.
4. ItuneSyncUIHandler.exe crashed (not sure the exact filename, it is someHandler.exe)
5. Restart iTune and outlook.
6. Sync again, works. iPhone Calendar is empty.
7. Added 1 new entry to Outlook, sync, worked.
8. Added 1 new entry to iPhone, sync, worked.
9. Outlook, File->Import the newly created PST.
10.Sync to iPhone: Failed. Outlooksyncclient.exe crash.
11. Remove all and re-import categories one at a time until Outlooksyncclient.exe doesn't crash.
12. Found the problematic category. Further narrow down the problematic entries by importing a few entries at a time.
13. Remove problematic entries. Works!

I have some really large entries (contains long paragraphs in the note section)
The sync goes fine once I removed them.

Good luck everyone! 🙂