Windows 11 won't install those 25 year old programs anymore. Wine will.
this post was submitted on 28 Jan 2026
701 points (95.1% liked)
Programmer Humor
29074 readers
1087 users here now
Welcome to Programmer Humor!
This is a place where you can post jokes, memes, humor, etc. related to programming!
For sharing awful code theres also Programming Horror.
Rules
- Keep content in english
- No advertisements
- Posts must be related to programming or programmer topics
founded 2 years ago
MODERATORS
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, 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
load more comments
(1 replies)
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...
Narrator: but it doesn't.
“Should” does a lot of heavy lifting in that sentence. 🤣
load more comments
(5 replies)
Depends on the program. I've got a handful of that old on CDs that still install fine. Checked when I was backing them up to ISO. There's little bits of weirdness and unintended behavior while running them now, but they still install and run to a fairly acceptable degree.
That experience varies wildly though. Wine tends to handle things better and more consistently.
Windows sucks, but I made some tools 20 yrs ago and they still just run in win11. As they did on all other windows before since...I dunno, 95? Or 3.11?
But anyhow: Windows sucks.
load more comments
(5 replies)
I never tried this but your comment made me wonder: there are probably some programs that run better using WINE in WSL than running them directly in Windows 11.
load more comments
(4 replies)
macOS, can I install this 2 year old program?
No, the architecture is no longer supported in this version of macOS
"no because the dev hasn't paid us to certify it as safe so you'll have to jump through 37 hoops in order to allow you to right click, hold options, and click open. THEN we'll give you an option to install it"
Is this a LibreWolf on Mac reference, because I hate this so much about LibreWolf on Mac lol.
Not so much a librewolf reference as much as a "any app you download from the Internet" reference lol
I'll have to try installing librewolf when I'm feeling frisky though
load more comments
(3 replies)
I mean, macOS has a lot of issues but the one hoop needed to run any unsigned app is "right-click app icon, click open".
Wait, you guys can right click now?
Yeah, shocking you can choose whichever mouse you want and probably have been able to since USB mice became a thing.
Even when apple mice didn't have two buttons, you could right click via control + click.
I should probably get out more
Sometimes it won't let you even get to that step without going into the settings and finding a secret security notification that it blocked it from opening
Yeah, and in rare instances, you’ll need to take the app/binary out from the quarantine
load more comments
(3 replies)
load more comments
(1 replies)
load more comments
(10 replies)
Windows, can I run this 25 year old software I just installed?
In the early 2000s there was this website called dll-files.com or something like that, and every time that error popped up (which happened a lot in the 90s and 2000s), you'd go to that website, download the missing file, and 99% of the time it would fix the problem. These days I'd advise against obtaining random DLL files from the internet but back then it was like magic.
Or you'd get lucky and some other program you installed happens to have the right dependencies. Just copy them to the application install dir or to C:\windows\win32\ and off you go.
load more comments
(2 replies)
Legit, at my current workplace one of the first things i did was update the very neglected hardware.
The IDRAC on the core server was so old i had to spin up an xp vm just to get a browser that would accept it so i could upgrade.
Yeah, stuff like that continues to be the best use-case for windows virtualization. Sounds a lot like trying to upgrade the BIOS or Firmware on an older PC; often the installer is some binary that only runs on Windows of the same vintage.
Backwards-compatibility with older web browsers so engineers can build websites for them, is another. I've also heard of industrial automation (e.g. CNC machines) being married to Win2k or WinXP, so being able to run an old OS on new hardware is crucial.
load more comments
(1 replies)
load more comments
(3 replies)
Wine: Just choose from a big list of overwrites.
load more comments
(1 replies)
As a programmer, it's pretty wild how much of Windows under the hood has remained completely unchanged. I started writing software synthesizer applications back in the late '90s, using a part of the Win95 API called "winOutX". The functions are kind of clunky to use but they allow you to programmatically create your own audio buffer arrays filled with whatever sounds you're up to creating and dump them into the playback stream for seamless audio. This shit has remained in place, working pretty much perfectly, for the last 30 years. It was even there in WinCE/Windows Mobile, which allowed me to write software synthesis applications for early smartphones circa 2005. And it's still all there today.
I like to rip on MS as much as the next guy (not least for them completely dropping the fucking ball as far as smartphones were concerned), but sometimes their incredibly long-term conservatism can work to your benefit.
load more comments
(7 replies)
Nope, can't find this ancient version of libc!
You can still compile it against the modern version.
And if it's static linked it will either run or you can ask Linus to murder someone for you.
I was trying to compile the first version of SuperTuxKart just for fun, how naive I were... Nowadays it's like translating ancient runes and good luck finding those ancient libraries
load more comments
(3 replies)
load more comments
(1 replies)
"Old tools" does not mean obsolete or bad. It means tested, hardened, and reliable. And crucially, probably runs in a couple megabytes of memory, which you might need if the cost of RAM suddenly quintuples for no reason.
B-but don't you want AI in vi?
AI in vim is actually often convenient.
:set ai
Cool, now it will keep track of my indentation.
Now sometimes that gets in the way, and while you can:
:set noai
Usually it's best for me to:
:set paste
And that's my take on the utility of AI in vim. (that is what you meant right, there isn't some other AI people are thinking of right?)
load more comments
(1 replies)
load more comments
(1 replies)
I wanted to do the cool neofetch thing all the femboys in thigh highs are doing. Shits already installed on mint. My boring ass win98 clone is doing the femboy thing no questions asked.
Interesting. Neofetch has ceased development but fastfetch is here to take its place though.
load more comments
(3 replies)
Hey. The cool transfems in thigh highs are doing it too.
Initial release of dd was for Unix in 1974 and it's still updated for use in modern systems.
I used it just the other day and it was already installed.
My issues are not install, but uninstall. Why do I have so much crap installed? I used it on a project once 7 years ago and haven't since. Why not uninstall it? It is useful, just not currently. It took less than a minute to install when you installed it the first time and your connection is faster now? But what if the archive goes down or it is retired or obsolete? It is small, keep it!
Turns out lots of small adds up to big.
load more comments
(7 replies)
Slackware moment
Roller Coaster Tycoon came out in 1999 but I notice it didn't come preinstalled on Mint. Is my install broken? /s
Sorry, only 25 year old software included. You're on your own for 27 year old software.
And this is...bad? Or do you mean it's lying?
I think this is just a really terrible use of this specific meme format. I have no idea exactly what OP was trying to get out with this. I'm still confused whether this was a good or a bad thing.
load more comments
(1 replies)
view more: next ›