If you're having difficulty syncing your contacts or calendars to iPhone or iPod touch with iTunes for Windows via USB, this article can help. Note this article does not apply to wireless syncing with Exchange ActiveSync or MobileMe.
iPhone, iPod touch, iPhone 3G, iPod touch (2nd generation)
Syncing contacts or calendars to your iPhone or iPod touch requires that the latest version of iTunes is installed. Refer to "iPhone and iPod touch: Minimum system requirements" or the iPhone Users Guide for supported contact and calendar software on your computer.
If you find that some of your data syncs to your iPhone or iPod touch, but you see an unexpected number of changes or modifications, you may need to reset your sync history. This causes iTunes to prompt to Merge or Replace information on the device when you next attempt to sync your information.
To reset your Sync History:
Open iTunes.
From the Edit menu, choose Preferences.
Click the Devices tab.
Click the Reset Sync History button.
If the issue continues and you know all of the data is on the computer:
Reset the Sync History again using the steps above.
Select the device in iTunes and click the Info tab.
Scroll down to the Advanced section and under "Replace information on this iPhone/iPod" select Contacts and/or Calendars.
Click Apply.
If the issue continues and you know all of the data is on the iPhone or iPod touch:
Reset the Sync History again using the steps above.
Remove all of the contact and calendar information from Outlook.
Select the device in iTunes and click the Info tab.
Scroll down to the Advanced section and under "Replace information on this iPhone/iPod" make sure Contacts and Calendars are not selected.
Click Apply.
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