Why won't iTunes and my iPhone 4 cooperate with each other and sync my calendar?

Hi mshealy2,

Welcome to the Support Communities!

What type of computer do you have? Do you have an iCloud account? That is really the best way to keep information synchronized between your computer and devices.

The information below will show you how to set it up:

Apple - iCloud - Your info up to date on all your devices.

http://www.apple.com/icloud/features/

iCloud Help: What is iCloud?

http://help.apple.com/icloud/#/mmfc0efea4

Apple - iCloud - Learn how to set up iCloud on all your devices.

http://www.apple.com/icloud/setup/pc.html

I hope this information helps ....

Happy Holidays!

- Judy

If you have updated to Mavericks, you can no longer sync your calendar through iTunes. You'll need to use iCloud.

You can buy the Mavericks Server for $20 and then sync locally (but still wirelessly). A search of the forums will turn up other threads with other suggestions.

Best of luck.