After numerous syncs with iTunes on multiple computers, all the calendar items on my iPhone were screwed up. Sometimes it was off by as much as a day. Sometimes I had duplicates on both days. Instead of manually deleting all the items by hand, I just decided to wipe the whole thing and start over again from a fresh sync. After some failed Google searches, I figured I’d just give it a try. It’s simple. Here’s how on Windows with MS Outlook (but I’m sure it works on Mac OS X if you substitute the appropriate steps).
- Create a new, empty calendar.
- Connect your iPhone and open up iTunes.
- Click on your iPhone in the Devices list in iTunes.
- Go to the Info tab.
- Check “Sync calendars with” and select Outlook.
- Check “Selected calendars” and check your blank calendar.
- Uncheck “Do not sync events older than” and I put 0 days just in case.
- Scroll down to the Advanced section.
- Under “Replace information on this iPhone”, check Calendars.
- Click Sync or Apply and you’re done.
Here’s some screen shots for visual reference (it’s what I’m seeing anyways).


THANK YOU!!! I’ve been trying to figure this out for a month. Great instructions!