It’s a bit complicated. 
It’s down to Steinberg, not Microsoft, and is a bug that has become more prevalent since Cubase 14.0.40.
In short, the problem is that MIDI Remote settings are also saved within projects.
When you open old projects, this can lead to issues such as duplicate entries or the MIDI Remote controllers not being recognised.
Often, the controller assignments in the global mapping file are reset.
Since Cubase 15.0.10, at least the assignments are no longer reset. However, problems such as duplicates can still occur when opening an old project.
I think the problem lies in the fact that the old project still contains code from the bug, causing the otherwise functioning MIDI Remote to crash.
You can find the full story with suggested solutions here.
It’s worth reading through the whole thing.