PDB Files won't load for some projects

I have a project with multiple references to my own code in other dlls. One of the dlls loads its pdb file when I run the website, and the other doesn't.

From Output I see this:

LOTS_OF_TEXTShared.BusinessLayer.DLL'
LOTS_OF_TEXTShared.Visual.Utilities.DLL', Symbols loaded.

I double checked and they both have the corresponding pdb file in that "LOTS_OF_TEXT" location...but one of them loads the Symbols (and allows debugging) but the other doesn't.

Why? How do I get the Shared.BusinessLayer.DLL to load Symbols so I can debug it?

EDIT
For reference sake, I have Belvedere copying the pdb files to /AppData/Local/Temp/SymbolCache when they change...which is where my Debugging settings tell Visual Studio to look for Symbols.

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Start a vsvars cmd prompt (or powershell) and browse to the LOTS_OF_TEXT folder. Visual studio ships with a tool called 'dumpbin.exe' that allows you to examine the structure of a .dll or .exe. To look for debug symbols, run dumpin in the cmd prompt by typing dumpbin /headers Shared.BusinessLayer.DLL and you should see the symbol path in the header information for the dll if it was actually built with symbols. As long as the symbols are there, or on the search path, they should be loaded.

That being said, check that visual studio is set to loading all symbols by going to Tools->Options->Debugging->Symbols and ensuring that the 'Automatically Load symbols for:' radio button is set on 'All modules, unless excluded' and that the exclusion list doesn't contain any relevant images.

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