App not opening after installation with wine on the Linux terminal of a Chromebook

[Martinsij70]

I used wine to install two windows apps from my Linux terminal (using their exe files) on a Chromebook. The installation was successful and I can even see the icons of the apps in my Linux apps folder. But the app opened only once which was immediately after installation. After that, it didn't open at all.
Please I need help with this as the app is very important and it's urgent. Thanks

[MeowImmunecat]

What apps are they? Can they be tested for free?