Crash dump – WinDbg – force PDB files to match doesn’t work

The ChkMatch utility is designed for this exact scenario. As long as you have the original .EXE, you can recompile the sources (with the same compiler and compiler settings) and patch the new .PDB to match the old .EXE.

In this example, OriginalExecutable.exe is the executable that no longer has a .PDB file, and RebuiltPDB.pdb is one that has been produced by rebuilding the original source.

chkmatch -m OriginalExecutable.exe RebuiltPDB.pdb

Now, as long as the two files have their original names, The debugger should accept them as a matching pair.

It sounds like you want to use a Symbol Server so that WinDBG or VS can pull down symbols that correspond to the build of the library you're debugging. If it's a third party component and you have private symbols you can either put them symbols in your own server or see if the third party has a public symbol server.

Windbg won't load symbols if they don't match the dll you're debugging, you can use !sym noisy to see more about the symbol loading process. If you choose not to use a symbol server you can manage all the pdb's by hand and load them manually into windbg (use lm v to get detailed information about a module loaded in your process)