Yup, we’re on this topic again because I keep hearing people complain that they are unhappy about how to sync Outlook in a non-Exchange environment. But this time Microsoft has provided a tutorial which also covers photo syncing for contacts (uhm or lack thereof). These may not be new to you, but certainly there’s still a lot of questions about this issue (and why it’s so freaking hard for a company who created both Outlook and Windows phone to tie the dang things together seamlessly). Here it is in full:
If you’re using Outlook without Exchange, you can get your Outlook-based contacts onto Windows Phone 7 by using one of the following methods:
Note While you cannot sync contacts directly from Outlook to Windows Phone 7, you can move or sync Outlook contacts to a service such as Windows Live. The methods below describe how to move Outlook contacts stored on your computer into Windows Live. Contacts stored in Windows Live will automatically sync to Windows Phone 7 once you add that Windows Live account to your phone.
Important: Contact photos stored locally (on your computer) in Outlook will not sync to Windows Live using the methods below. You’ll need to add your contact pictures manually on Windows Phone 7, since Windows Live doesn’t allow for assigning of pictures to contacts outside of "network contacts" (Messenger). This may not be an issue if you have that same contact as a Facebook friend and have linked the contact cards on the phone; the Facebook profile picture would then become the contact photo.