When I set a breakpoint on one of the methods that appears on top of the stack (!CLRStack), I get lots of these messages for every DLL that the debuggee is referencing including the .NET Framework ones.

ERROR: Module load completed but symbols could not be loaded

Further digging into this shows that windbg is not loading every .pdb file that I make available in the symbols path. I've double-checked my symbol's path and it looks OK, but the following commands clearly show that not all PDBs are loaded correctly!

0:000> !sym noisy
noisy mode - symbol prompts on
0:000> .reload
Reloading current modules
................................................................
DBGHELP: ntdll - public symbols
c:\symbols\ntdll.pdb\6992F4DAF4B144068D78669D6CB5D2072\ntdll.pdb
..
0:000> .sympath
Symbol search path is: SRV*c:\symbols*C:\xc
Expanded Symbol search path is: srv*c:\symbols*c:\xc

I've c:\symbols being used for the cache and c:\xc being used for the .NET app PDBs that WinDBG seems unable to find. Any idea how I can use to help further troubleshoot this?

Thanks