IPhone 4 no longer syncs with Outlook

Until a few days ago I was able to use iTunes to sync my iPhone 4 contacts and appointments with Outlook. I used a USB cable, and the sync was completed quickly and correctly every time. Now iTunes hangs during the sync process most of the time, and when it does indicate that the sync has completed, no data was actually transfered. I am using a USB cable for the transfer between the iPhone and a PC running Windows 7, and have all the latest software versions installed for iPhone, Outlook, and iTunes. I have reset the iPhone's sync history and rebooted the PC several times. None of the troubleshooting steps on apple.com appears to help. I would be very grateful for any assistance the community may be able to offer. Thank you!

Your cynicism is spot-on. I have tried everything that you tried and more. My contacts and notes do not sync either, in addition to my calendar. But, music, photos and apps do sync. After spending over two hours with Microsoft I am convinced this is a bug in the iTunes sync software, but Apple does not seem to understand that if they create syncing software that is supposed to connect between two different devices, that they either need to own the handshake or be able to say why the sync can't make the handshake. They just keep saying, "It's an Outlook problem." Agree with you about Androids and Blackberrys (although I so loved my Blackberry, I am still heartbroken to have had to give it up). I believe that the only solution is now going to be some form of cloud sync - either to use the iCloud Control Panel for Outlook sync, or to create a Google calendar and sync through their cloud, or to get on MS Exchange through MS Office 365. Or hope that iTunes decides to acknowledge the problem and release a bugfix in iTunes. I also heard that they will not support Office 2010 iTunes syncing at all. I doubt this because I know people who are doing it. Anyway, sorry for long post, appreciate the help.

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p

Hi P,
Make sure you have the latest version of iTunes and Outlook. You can download the latest version of iTunes here: http://www.apple.com/itunes/download/
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Apple doesn’t routinely monitor the discussions. These are mostly user to user discussions.
Send Apple feedback. They won't answer, but at least will know there is a problem. If enough people send feedback, it may get the problem solved sooner.
Feedback
Or you can use your Apple ID to register with this site and go the Apple BugReporter. Supposedly you will get an answer if you submit feedback.
Feedback via Apple Developer

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Hey, man. Sorry I have no solution, but it may not hurt to know you are not the only one.
I uprgraded a 3GS to iOS 5, set it up to sync with iCloud initially, and then switched back to sync with PC as before. It seems that my calendar was syncing at first, but within a few days it just stopped.
I also recall a ton of weird "sync conflicts" that I had to resolve, even though the iTunes conflict reslover showed information that was identical in Outlook and iPhone calendar.
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I have never given nearly as much thought to Android as I have lately.
It may be time to call Apple Support, but my previous experiences with them (and the "Geniuses" at the store) were underwhelming.

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