DLL fails to update when a PDB file is present

Unity: Scripting Buildtime

6.2.X

6.1.X

6.0.X

2023.3.X

2023.2.X

2022.3.X

2021.3.X

How to reproduce:
1. Open the attached project "CodeBase.zip"
2. Observe the Console

Expected result: No errors are present in the Console
Actual result: "Unable to update following assemblies" error is thrown in the Console

Reproducible with: 2021.3.34f, 2022.3.19f1, 2023.2.9f1, 2023.3.0b5

Notes:

The error sometimes fails to show up, however, upon loading up a fresh copy of the project it shows up