Welcome to the forums. It seems syncing with Outlook is a known issue. I haven't found a fix yet.

Personally, I think this version of DM is quite unstable. It gives errors, doesn't sync, doesn't always load Media Manager....4.2 SP2 is much more stable. For anyone using a 4.3 device (the 8130 so far) you can still use DM 4.2 SP2.