I didn’t know that: the VS2008 debugger has many bugs. Specifically, if you have a solution with multiple websites, debugging doesn’t work!
Symptom: Upon reaching a breakpoint, StepOver/Into do not work, but resume execution. This makes the debugger pretty pointless.
There is an update for this available since february the fourth, 2009(!). I’m wondering why this was not distributed via Windows Update. Anyways, here’re the links: