I encountered a weird thing about debugging in Visual Studio 2005 Professional. You could try it in your VS. May be it is a bug.
1. Make sure the "Debug" toolbar is dragged out. All the operation is on it.
2. Set a breakpoint.
3. Start Debugging from the Debug toolbar, wait until reach the breakpoint.
4. Stop Debugging and immediately Start Debugging. After you stopped debugging, it will take about 1 second that the "Stop Debugging" becomes unavailable. Just IMMEDIATELY Start Debugging when it is still available.
5. Now you would notice:
1) Program stopped at breakpoint;
2) Continue Debugging is unavailable (which should be available);
3) Pause Debugging is available (at breakpoint, it should be unavailale);
4) Stopping Debugging button is highlighted, available and unclickable (so weird huh );
5) All the "Step" buttons are unavailable.
Now, just wait a few seconds, the "Stop Debugging in Progress..." window would appear, and halt forever! You must click "Stop Now".
Notice that, although when the Continue Debugging button in the toolbar is unavailable, the corresponding button in the menu is still available, and act right.
Yes, this is not a big problem, but when I want to stop and start debugging quickly, it becomes very troublesome. I think this may be just a IDE bug.

Debugger's Bug?
Orjan Lindberg
Mohamed Kishk
What I was trying to say is that the "work-around" is simply to wait until the Stop debugging toolbar button is disabled before re-starting debugging. That should indicate the debugger has properly terminated debugging the process. But I suspect you already knew that.
Simon Harriyott
Bimali
But also, because it is likely a race-condition bug in the event-handling code, the fix may not be as trivial as it might seem and there is certainly the potential to break more than is fixed if we change it at this point.
talshac
Which language are you debugging C++, VB, or C#
Neil
ersin sivaz
That doesn't suprise me. It is likely a bug in debugger code common to all the VS 2005 products.
Thanks again for reporting it.
khanhpt
I've moved this post to the C++ forum, as they own C++ debugging and should be able to assist.
Neil
PDagent
Thanks for taking the time to report this. I have verified the behavior you've seen. It is definitely a bug in the debugger (or perhaps in the connection between the debugger and the IDE.) I have entered it in our bug tracking database.
The work around besides simply waiting until after the stop debugging toolbar button is no longer enabled which should indicated the debugger has properly finished terminating debugging the first process.
mmmeee
Seems this "bug" also exists in Team Suite edition...