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Using WINE for non-Game Programs

I have a Surface Go tablet that I switched over to Linux a while back, and just came across a problem that I don't know how to approach. I use an iDataLink Maestro module in my car to make an aftermarket stereo do what I want it to do. I want to check for a firmware update on it, but the management software tool is windows or mac only.

So I installed WINE and the PlayonLinux front end. I successfully installed the tool (Weblink) but the keyboard doesn't work so I can't log into it. The trackpad works though, and this is a directly connected keyboard/trackpad, so for one to work but not the other seems weird. I can find threads about non-functional keyboards with some games, but I honestly don't understand the guidance being dished out.

How can I troubleshoot and fix this keyboard issue?

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