Originally Posted by BKPruitt
Windows Live doesn't seem to do contact photos for some reason. The only way I've seen a contact photo come through Windows Live is via MSN Messenger accounts - not exactly a convenient option, in my opinion.
That said, if you're open to using Google, you could use CompanionLink to sync Outlook contacts (and calendars and tasks) to Google, then to the phone. You'll get all your contact photos this way. If you have questions about it, just let me know.
If nothing else, hopefully this saves you an expensive phone call to the psychotherapist! ;)