How does your build.bat look like? Do you have code for locking game reload while pdb file is created?
It might be the case described in Day 39:
https://hero.handmadedev.org/videos/game-architecture/day039.html (Fixing live code loading 0:52:38)
Basically Visual studio first generates dll, and your game notices that and loads it, but only after that Visual Studio creates pdb file. So when your game loads dll file Visual Studio debugger sees only old pdb file. New one is not yet created. That's why you don't see source information for dll.