Let's see, first of all to check the filter the alert is using, you can just create the alert with the user is working, and check the subscription data in the database "TfsIntegration" in the table "tbl_subscription".
Second, with that, you can try to create the subscrition in the command line using bissubscribe.exe, with the same filter and user, to check if the problem is in the Visual Studio IDE, or in the user, Team Foundation or something else.
I think you should try this, as it seems pretty strange this problem
Luis Fraile - MCSD.NET - http://luisfraile.spaces.live.com/ |