@jp734 :-
I suspect what's happened is this:-
The WINE-portables are designed to only 'link' into Puppy.....NOT to fully install. You have a directory in /root called .wine (note the "." in front of it; this is a 'hidden' directory). This is your WINE 'prefix', and is where WINE creates the emulated Windows file-system once it's run and set itself up.
Because you installed the repo version of WINE, this was a 'full' install. In other words, the /root/.wine directory is an actual directory. When you remove a WINE installation via the PPM, it removes the WINE components.....but it does NOT remove your 'prefix'. So; when you then 'installed' WINE-portable 9.20 via the 'LINK' script, it would have done everything it was meant to do, WITH ONE EXCEPTION; it would not have 'linked' the freshly-created .wine directory from the portable into /root.....because a sym-link CANNOT overwrite a standard directory.
An SFS package may have done so, because these work directly on the Puppy 'layering' file-system (older Pups used aufs, newer ones are now using overlayfs).....but even there I'm not at all certain. My set-up simply uses standard sym-links. 'Twould appear you must have created the progeCAD configuration stuff correctly within WINE's 'prefix', while you were running the older 3-series WINE from the repository, but for whatever reason it wouldn't actually fire up fully. Hardly surprising, since you were attempting to run a 2025 app under a 2016/17 build of WINE.
When you then 'installed' the WINE 9.20 portable, you were running a build of WINE that was also up-to-date.....so it was happy to run with the already-created progeCAD config stuff.
Make sense? Don't fret if it doesn't; WINE has been confusing people for many years.....and nearly every major distro seems to have its own unique way of installing/implementing it. (Just to muddy the waters further, like...)
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Out of curiosity, are you wanting to use this for working with stuff already created under another build of progeCAD, or was this simply an experiment with something you found while browsing? I'm only asking, because for 3D/2D CAD stuff there is a Linux-native alternative (it's pretty good, too!) I'm talking about
FreeCAD
It's available as an AppImage for Linux.....and it runs OOTB under any Puppy from Bionicpup64 onwards. And because it's an AppImage, I've turned this one into a 'portable', too..!
viewtopic.php?t=13152
Just a thought, like. Entirely up to you, of course.....but I thought you might be interested enough to want to take a look.
Mike. 