Yeah, Software protection was very naive in the beginning. Fun fact: I owned a windows 3.11 for workgroup UPGRADE disc collection, it was clearly explained and also enforced from the setup installer. So, no previous installed win 3.0 == upgrade installer will fail. The fix: just create an empty Textfile named win.com at any place - the installer simple scans the WHOLE disk just for this existing filename. Next fun fact: in reality, the Upgrade contained the full installation, no only a delta. Men, software was so simple these days....
I have a childhood memory of my dad buying a shrink-wrapped copy of the Windows 3.1 Upgrade that was supposed to allow any installation of "3.0 or earlier" to become Win 3.1. it turned out when we actually tried it it only accepted 3.x though. [1]
I think he ended up pirating a 3.x install from a friend and running the upgrade on to of that; felt pretty morally clear given what the box had advertised.
[1]: eg https://www.ebay.com/itm/376080245422