this post was submitted on 28 Jan 2026
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I’m really sorry to do this, but 25 years ago was 2001.
Now that the painful part is out of the way, 32-bit software from 2001 should work in Windows 11.
Oh cool, let me install this software, what, it won't install because it's missing quicktime? Oh it needs directx 8 runtime? That could be a problem. Let's advance the clock, 2004, that should be fine... What do you mean you can't run .NET 1.1 applications and so that won't run?
Ironically, wine is more likely to have a path to easily run those programs under Linux, but if you had a Linux binary from that era you'd likely have a hard time getting that to run, probably harder than the microsoft scenario. So old Windows software is more likely to run under Linux than old Linux software...
I ran into old software (for Windows XP), especially games not working even with compatibility mode used for the install and opening of the app. Now if the publisher or Steam or some party puts a tad bit of effort, then yes, those games can work, although I guess a big part of that is also hardware and driver related if talking about 3D games for instance.
Oh, it should work and it will if you put all the files in the right places yourself by say installing it on wine and copying the changes to the wine system directories over, but starting in Windows 11 running the installer gets a deliberate "this program isn't meant for this version of Windows" error.
Run the installer in compatibility mode, then run the application in compatibility mode?
Didn't work. Application doesn't even need compatibility mode to run. Running the app copied by someone else from their previous Windows 10 computer sorta works but didn't find files installed to system directories. Windows 11 just deliberately refuses to execute the installer probably based on recognizing the old family of installer programs specifically.
The users wanted a new Linux laptop. I installed LMDE, showed them how to run the installer with wine. It made a menu item. Drag and drop from whatever the cinnamon file manager is doesn't work, and there was no file association to open the program's files. I added one that just opens them with wine and lets it figure it out. I also showed them where their wine c drive was.
After a few weeks they wanted to print to pdf as well as their printer from wine and I had them install cups-pdf
You will run into a lot of old Library issues. Like elf binary missing, lack of 32 bit is starting to become a problem. If you have any old 2.4 kernel dependencies your probably gonna have a problem in Linux
My machines and my children’s machines will never boot Windows again.
Good! Not sure how that’s relevant, but good!