iTunes stopped syncing Outlook 2003 calendar (iPhone 4s, Win XP Pro)

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iTunes stopped syncing Outlook 2003 calendar (iPhone 4s, Win XP Pro)

I've been successfully syncing iPhone 4s with Outlook 2003 via iTunes since Feb-2012 (using Replace information on this phone for Contacts and Calendar).

As of May-2014 iTunes no longer syncs the Calendar (but syncs everything else). Not sure exactly when it started. Anything added to calendar Apr-2014 and earlier is in there, but "edits" to those events are not. It looks like the calendar on the iPhone is stuck at a particular moment in time. It does not update even though iTunes reports that it is "Syncing calendars" (see screenshots below).

I have tried every recommendation that I've found (apparently many people are having this issue with no support/resolution from Apple). Here are all the things I've tried (and wasted countless hours on) without success. I'm fairly technical but am at my wits end with this.

Sync with Norton Antivirus off
Turned off Symantec antivirus plugin in Outlook COM Add-Ins
Verified that iTunes Outlook Plugin is checked in Outlook COM Add-Ins (iTunesOutlookAddIn.dll)
Tried suggestions from https://discussions.apple.com/thread/5950688
By MartinHines posted 3/1/14 (** UPDATE 3 -- FINAL -- PROBLEM FIXED ***)
1. Uninstalled iTunes for Windows (and associated Apple software) using this guide: http://support.apple.com/kb/HT1923 (did this in exact order)
2. Installed older verson of iTunes for Windows v11.1.1.11
3. Performed additional steps as outlined in 3, 4 and 5

Tried suggestions from https://discussions.apple.com/thread/5950688?start=15&tstart=0

By Calison posted 3/12/14

Close iTunes.
Do a hard reset on the device (not a restore!).
Go to Start> Services and stop and restart Apple Mobile Device (highlight and right click on it, so these options appear).
Go to Control Panel> Programs and Features.
Then find the following three programs, and for each one highlight, right click and choose Repair:

Apple Application Support

Apple Mobile Device Support

iTunes.

Restart iTunes, attach iPhone.

Tried suggestions from https://discussions.apple.com/thread/2369239?answerId=11242346022#11242346022

Moved all calendar entries created May-2014 out to temp calendar

Moved all recurring appts with no end date to Temp calendar; stopped and restarted Outlook, iTunes, AppleMobile service and hard-booted phone. iTunes does not even see "Temp" calendar. Also tried just 'Selected calendars' = Calendar (only one showing).
Have run iTunes diagnostics, nothing reported

Deleted iPhone backup and reset sync history

Outlook detect and repair

Outlook calendar turned of properties -> 'automatically generate Microsoft Exchange views'

Deleted iTunes iPhone backup, cleared sync history, turned off iTunes Sync Calendars with Outlook, said it would erase all calendars on iPhone which it did, calendar data gone on iPhone (still shows 'Calendar' in Calendars); then synced again with Calendar using option to Replace information on this iPhone (still doesn't show 2nd calendar in Outlook, just 'Calendar' default) - says syncing calendars as before and previous 'stuck in time calendar data' is back on iPhone (where did it get that from?).

Removed Local Settings -> Apple Computer -> Preferences directory (iTunes recreated it)

Removed My Music -> iTunes directory (iTunes recreated it)

Removed Outlook iTunes Outlook Plugin, launch iTunes dialog 'Please wait while Windows configures iTunes

iPhone 4S, iOS 7.1.1

Posted on May 16, 2014 4:16 PM

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Answer 1

ilober Author

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May 18, 2014 9:15 AM in response to ilober

*** SOLVED 5/17/14 *** After countless more hours I solved my problem. It turns out that one of my calendar items was preventing iTunes from syncing the calendar. Since I knew I had successfully synced prior to May-2014 I dragged all the calendar items for May out of my active calendar into a backup calendar folder (which I temporarily put under Deleted Items). The sync worked. I then dragged the items back in groups of 5 (arbitrary, rather than 1x1) and synced. This narrowed it down to 1 item ... which I looked at extensively but there was nothing unusual about it. It had a start / end, it was well-formed. I have no idea what caused it to create this sync problem.

After all the things I tried (outlined in original post) I decided to try to sync on a Win7 machine with Outlook 2010 using a backup .PST file from 5/3 that I had. It worked. I then copied my current/active .PST file from my XP Pro / Outlook 2003 machine to the Win7 machine and the sync failed. This is what led me to think of a problem with a calendar item. I realize not everyone has two machines to do this test but just wanted to provide some background as to how I got here.

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Answer 2

Jun 5, 2014 6:42 PM in response to ilober

Thank you for this idea. Had the same thing happen to me over the last 2 weeks using an iPhone 3GS and Outlook 2013... all contact, calendar, and note syncing failed. After reading your post and thinking a bit, I zeroed in on a calendar entry in which I had copied a picture in as the note. Outlook accepted that just fine... but apparently broke the sync. After removing the note (while leaving the calendar entry), the sync again worked.

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