This worked for me.
Greetings,
After spending 2+ hours on the phone with Apple technical support, here is what I found worked.
http://discussions.apple.com/thread.jspa?messageID=6412482�
Please see me post here in clear text: <let me know if this helps you at all>
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ATTENTION FELLOW IPHONE USERS / APPLE
I was having the EXACT same problem as the person who originally created this post... Downgrading to iTunes 7.4.3.1 absolutely fixed my Outlook > iTunes > iPhone sync issue.
FYI - This issue started right after my users upgraded to iPhone firmware 1.1.3 and iTunes 7.6. There may be some issue with the latest version/update of iTunes.
<Just a CYA, backup all the files/directories that are to be deleted here. -- Use this info. at your own risk.... However, it worked great for me.>
Here is what I did:
#1) Under Windows Add remove software, completely remove: iTunes, Apple Mobile Device Support, & Apple Software Update. - DO NOT REMOVE ANY BOOT CAMP SOFTWARE.
#2) Reboot PC (or Mac running Boot Camp - running Windows)
#3) Under "C:\Documents and Settings\<user account>\Application Data\Apple Computer", remove any reference to iTunes/Quicktime.
#4) Under "C:\Documents and Settings\<user account>\Local Settings\Apple Computer", remove any reference to iTunes/Quicktime.
#5) Under "C:\Documents and Settings\<user account>\My Documents\My Music\iTunes ", rename: "iTunes Library.itl" to "iTunes Library.old"
#6) Under "C:\Documents and Settings\<user account>\My Documents\My Music\iTunes ", rename: "iTunes Music Library.xml" to "iTunes Music Library.old"
#7) Download iTunes 7.4.3.1 from:
http://www.apple.com/support/downloads/itunes743forwindows.html
#8) Normally install iTunes 7.4.3.1.
#9) Once installed, Connect iPhone. GO under the "Info" tab under the iPhone device. Make sure that you have the setting to overwrite the Contacts and Calendars on the iPhone, under the advanced settings area. (remember, you will be overwriting any contacts/calendars that are NOT synced with the computer)
When you connect your iPhone you will need to totally re sync your Outlook Contacts and Calendars - FROM Outlook TO iPhone (overwrite). Also, you will need to rebuild/re index your iTunes library music.
This worked fine for me in my particular environment; however, if ANYONE has a quicker/easier way to resolve---possibly without downgrading to iTunes 7.4.3.1, LET ME KNOW.
You might want to do setups 1 - 6, and just try reinstalling the latest iTunes. If this works for someone, please post.
Thanks
Will