I have been happily syncing my Outlook calendar for the last 10 months with no problems. Around the same time, I upgraded from Outlook 2003 to 2007, updated itunes and the software on my ipod touch to 3.1.1. I am now unable to sync my calendar. The bar at the top that describes the sync says that it is syncing with the calendar, but nothing happens. I have left it for up to 10 minutes and then have to manually cancel the sync because it's not working. Does anyone have any idea why this is happening and how to fix it.
Same issue, using outlook 2007 and iTunes 8 w/out problems for month, but since upgrade to iTunes 9 and iPod Touch 3.1.1, nor calendar nor contacts do synch anymore. Going back to iTune 8 impossible because of library update..real nightmare..Apple MUST find a solution!!
I recently had a similar experience with my iPhone 3GS and Outlook calendar. The calendars suddenly quit syncing although Contacts and Notes continued to sync normally.
After unsuccessfully trying all of Apple's suggested fixes ("Troubleshooting the iPhone and iPod touch contact and calendar syncing via USB on Windows"), I discovered that inadvertently multiple calendars had been set up in Outlook. I removed the superfluous calendars and they began to sync perfectly fine once again.
In my case, I don't think was related in any way to iTunes updates, but rather user error. Now, I have two calendars in Outlook and two on the iPhone and my world seems to be 'in sync' once again.