I FIGURED OUT MY OUTLOOK SYNC PROBLEM.  TRY THIS.

I spent about 5 hours on the phone with 3 different apple tech specialists with no luck on how to get my iPhone to sync with outlook. My calendar and contacts would not come over to the phone. This morning I was trying to figure it out and I DID!
In Outlook:
go to tools->options->other tab->advanced options->COM add-ins->then check the box "outlook itunes sync add-in". Please post comments to see if this helped.

I saw this in another thread but it's worth duplicate
threads. Anyone with sync problems needs to do this.
Yes but Outlook 2003 disables one of the add-ins which causes Outlook to crash when you load program. Then the add-in is disabled and you can't enable it just by selecting the box in tools>other>advanced>com add-ins because it won't happen.It just keeps unchecking itself.
Here's what to do: with outlook open go to "about Outlook" You'll see a button "disabled components" under that will be the offending iphone addin. RE-enable it. Then do the manouevre I mentioned in second sentence. Then sync iphone and all contacts, calendar etc will sync to phone. BUT the next time you start up Outlook it will tell you that the addin causes a serious error and will disable it. I guess we will have to enable it each time we want to sync for now -Microsoft had no idea (nor did Apple) after several hours on support lines. God only knows when and who will fix this. This seems to work for now however.
Dell, Mac   Windows XP Pro  

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