The fix for this problem was pushed out to the servers om Dec 18 2011 and verified as working on most of the server clusters. If you are still having problems, let us know.
We're been seeing reports over the past few weeks that Outlook Connector is not downloading old mail. This is caused by a bug on the server-side where only mail going back a few months is downloaded. Only accounts newly created in Outlook or Live Mail are affected and if you remove and re-add the account, more of the older mail is downloaded. Patience is always a virtue: waiting through a few sync cycles may also download the missing mail.
The good news: this bug should be fixed this week.
Published Dec 7 2011