Visual Studio breakpoints do not load for the game project

I have a long-standing issue of breakpoints not loading specifically for my game project(s). This has been an issue in UE4 as it is in UE5, across multiple game projects and also different VS version (2019, 2022) as well as Rider. I have read other threads with this issue but haven’t seen any with this particular issue. I have the VS plugin installed. I am also building the engine from source.

Debugging has worked briefly for a time in both UE4 and UE5 before disappearing. I can set breakpoints that trigger in engine code just fine.
Looking at the Modules tab the cause of all this seems to be that the game project DLL is not recognized at all. I can find all other DLLs show up with symbols loaded which explains why everything else works but there is no “UnrealEditor-MyGameProject.dll” in that list. I have completely run out of things to check and have absolutely no idea why this happens. I’ve even tried building and running on a different computer and ran into the same issue (logged into the same account in VS so perhaps something bad in the synced settings?).