Application works with Wine, but not with Bottles

[31JSON]

I use a couple of Windows or macOS-only pieces of software for chemical research. I've gotten all of them running with Bottles except one, ChemDraw 23. I have it running in Wine using the instructions posted on WineHQ. I would prefer to use it in Bottles because the installation procedure is, to me, more straight forward. I think Bottles would be better to use on computers in my department. I was able to use the native installer to get it installed (which you can't do with Wine), but the app itself seems to silently crash when it's run. On the first run, I would expect it to ask for the product activation code, but it doesn't. Running it with the terminal open doesn't reveal any relevant error messages. It just seems to quietly die.

Is there any way I could diagnose this? It seems strange that it would work with Wine and not Bottles?

[bmp192529]

I got it working myself once once on my personal machine in Bottles and wasn't able to subsequently replicate it. I'm actually not completely sure how I got it to work; it was just one of those things where it didn't work, I gave up on it, came back to it a few days later, and it randomly started working. I am now trying to install the updated 25.5 version, which didn't work in bottles. Well, it installed, but wouldn't launch ChemDraw. It would launch Chem3D and everything else, though. I've found ChemDraw's license checking method to be VERY finicky. You may have luck if you delete the license.ini file to force it to ask about the license on launch. But as for why that that's only a problem with Bottles and not wine, I am not sure. I know definitely the .NET implementation in Bottles is not as good as that from winetricks, so that's probably part of it.