That's strange, it's sad you can't play these games :(
Viewing post in Underground Railroad jam comments
The itch install failed for me also but direct download worked. I've had the opposite happen too for other entries - direct download fails, but itch download works.
I though maybe it was because .rar was assigned to be opened by a Corel app but I reassigned it to 7zip and it still wouldn't work.
I think I had these issues in HAGJ4 too so I think its an issue with the itch app.