Jim Gries, absent too long from his blog at Gooey Bugs, puts up a nice post with some insight as to why you need the PDB files from the exact build you created your binaries with in order to use the debugger.
You ought to think hard about building PDBs even for your release versions and archiving those with the released binaries.
Check out Jim’s past posts, including his series on Debugger Tips, Tricks, and Tools. It’s been a long time since I read through those, and I’m finding a lot of useful stuff there.
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