Hi, I'm looking into this. I'm guessing it's because the last Windows build of Playscii was built from my Windows 10 desktop with a version of PyInstaller (the program I use to turn my Python into a runnable Windows EXE) that changed something about its compat status. I no longer have access to any machines running Windows 7. I'm going to search PyInstaller's issue tracker thoroughly and file a ticket with them if I don't find anything.
Obviously Windows 7 is no longer an officially supported-by-MS OS but I'd like to exhaust every other option before I tell everyone Playscii for Windows requires win10.