There might be multiple issues at work there, but one reason I can think of is that I still do Playscii Mac builds with 32-bit Python on macOS Yosemite, and 32-bit stuff stopped being supported with Catalina. I need to research what options are available to me to support newer macOSes.
Update: no actual progress on this, but here's an issue I have open with the PyInstaller project, which I use to create the Mac builds: https://twitter.com/playscii/status/1470155468395847683
I will let people know in this thread when I get it resolved - no ETA on when that will be unfortunately.