Crafty Blog

When I first got my iPhone, it would sync my Outlook contacts/calendars in iTunes when the phone was connected, and everyone was merry. Then, one day,  I noticed that events I had added in Outlook would show up after a sync, but events  added on the phone  would not show in Outlook. I had also noticed that when iTunes showed “Syncing calendars” during a sync, I would get an error about the outlooksync.exe app was crashing after about 30seconds.

After consulting the (un)mighty apple.com support pages and following all recommendations it had to offer, I was about ready to give up. While poking around iTunes sync settings in one last desperate attempt, I found a button called “Reset Sync History.” Out of curiosity (and since I didn’t have much to lose anyways), I clicked it. Immediately I plugged in my iPhone to see what I had done, and much to my surprise, the sync worked! It even prompted me for the events I had later added when it was not working, and were never synced in the past because of it.

So for anyone out there experiencing the outlooksync plugin crashing when syncing calendars on the iPhone, here are the steps to correcting it:

1)Unplug iPhone from computer

2)Fire up iTunes

3)Go to Edit->Preferences->Syncing(Tab), and click on the “Reset Syncing History”

4)When prompted, click “Reset Sync History” on the new window. Plug in your iPhone, and sit back while iTunes magically re-syncs everything!  You may get prompted for any events that need to be added locally (in Outlook) if they were created on the phone.

I have not tested this with the iPod Touch, but I would assume it would work on that as well, since it is basically an iPhone without the GSM radio

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