C# - Revit API - How to debug multi-version Plugin for Revit?

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I'm trying to debug my multi-version plugin for Revit however I'm having issues. It was originally created for Revit 2018 so it debugs fine in that, however when I switch the external program to Revit 2019.ex3, the program runs but none of the breakpoints are being hit.

I currently have 2 different debug configuration files. One for revit 2018 and one for revit 2019 which is what i would imagine the correct path to go.

When I look at the breakpoints while debug is running, I see The breakpoint will not currently be hit. no symbols have been loaded for this document.

I've tried loading the matching family symbol file but that when selected, I get the following warning:

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When I look at generating a new .pdb file, I've found that the pdb file that can be used is only the one that was created with this file.

How can I can I enable debugging for both versions in revit?

All help and/or direction is appreciated.

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