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After much work reinstalling Vista and Visual Studio 2008, I found out that I still can't debug 32bit MMC 3.0 snapins in Vista 64. You still need to attach the debugger manually to the running process. Unfortunately, this means that you won't be able to debug stuff while your code is loading.
I really was not ready to go back to 32 bit, so I compromised by creating a VMWare image that contains Windows XP SP3, Visual Studio 2008 SP1, and all the other necessary dev tools.
I now have a rig that I know always lets me debug. TortoiseSVN makes it simple to keep my VM and desktop synched.
Score that a WIN!
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COMMENTS
I recently struck this problem with VS2008 on Windows 7 x64 as well.
I eventually found a solution :)
The solution is to directly use the 32 bit version of mmc at this path:
C:\Windows\SysWOW64\mmc.exe rather than the one in System32.
you still need the -32 flag as in your screenshot.
When you try and debug via "C:\Windows\System32\mmc.exe -32" what actually happens is the debugger attaches to the 64bit version which starts the 32bit version(in SysWOW64) and then closes itself hence why it stops debugging immediately.
Thanks for the tip! Sorry it took so long to get to your comment.