I tried everything from re-installing/repairing VS 2008; installing SP1 as well. Nothing seemed to fix the problem.
After some time chasing down wrong errors on my output window, I finally decided to call it quits and post on StackOverflow, hoping the community could help me figure out the solution.
Sure enough, one of the questions already posted brought me to the solution.
Apparently this is a known issue, the gist of which is the following:
- Breakpoints in parallelized loops are eventually ignored after multiple hits
- Stopping and starting threads causes breakpoints to be missed
- Visual Studio may crash when you debug multiple processes at the same time
- Stepping over a disabled breakpoint when you debug a native application turns into a "go"
- Stepping when you debug a managed multithreaded application can randomly turn into a "go"
- Running the "Step Over" command while you are debugging multiple processes causes a deadlock
The one in red above was my exact problem.
Thankfully, there is a fix for it which can be downloaded: Fix for Visual Studio 2008 debugger not working
Once using the above said fix, I came across another issue:
Loaderlock was detected
Attempting managed execution inside OS Loader lock. Do not attempt to run managed code inside a DllMain or image initialization function since doing so can cause the application to hang.
After a bit of investigation it looks like some other running applications might cause this problem. Of what I saw the most, many people seemed to be complaining about iTunes. The other software I noticed causing this was grooveshark (flash since it is what grooveshark is based on. GrooveShark itself does not cause the problem).