Oldest GUI application that still runs on Windows 11

One crucial part of my role as my family's de facto IT support was making sure my mom's FreeCell score record (which was just a Windows registry value) made it from each computer to the next across countless upgrades. She hated the new version that came out somewhere along the way because the card decks changed. (Windows 7? Windows 10? I switched to Linux full time in the XP era so my memory is a little fuzzy.) So I made sure to keep a backup of the Win32 version she was used to, and loaded it onto every machine she ever owned. It wasn't quite the 33 years of its lifetime, but probably close to 30.

Mom passed earlier this year, so the FreeCell score record won't ever increment again, but I still made a point to back it up one last time when going through her desktop this summer.

I deplore the day we lost the menu bar and replaced it with "mobile first" designs. The desktop UI was perfected around the time of Windows 95 and has gotten worse with every iteration since then. That, and the increased reliance on non-native frameworks and libraries instead of working with directly with the Windows API in C.

This is one of those moments you are surprised to learn when someone has discovered something you just knew.

Freecell was the demo app in Win32s for Windows 3. It is thus several years older than NT as a retail OS.

I have downloaded Win32s and extracted Freecell from it, just to play the game on Win10 LTSC and Win11. Probably more than once in fact.

The default Freecell in 21st century Windows is an ugly blinged-out mess, and in minimal installations, there are no games at all. This is the quick easy way around it.

I just resurrected a 90s kids CD-ROM game that shipped for Windows 3.1 - https://github.com/matthewbloch/orlys-draw-a-story-fixes

The finished patch DLL ended up being a tour of the stuff that broke.

The game did launch on Windows 11 but the main issue was that the 8-bit pre-DirectDraw behaviour was broken - for 256 colour screens, Windows 11 resolvesld palette indices only once, but the game relies on being able to change the palette for fades etc. Most of the screeen ended up black, but you could see the animated parts just fine.

So most of fix ended up being to hook every draw call and implement a virtual GDI that acted like a graphics card of the day.

There was a 32-bit disc space check that overflowed, a couple of use-after-free crashes and some racey threading calls that can't have been tested on a machine with 2 CPUs.

Backwards compatibility from Microsoft was almost all there, and probably would have kept Orly running for a couple of subsequent Windows releases. But it relies on a developer meeting them half-way, it's not an emulation layer.

I like that we are amazed by this. And yet all of my books from 34 years ago open up just fine (without cheating, no book opening emulator required!). I can even open a book on my shelf from 1896 without emulation. Not trying to troll too hard but I do think it is shocking how accustomed we've gotten to zero backwards compatibility in the world of software.

I'm reminded of this amusing and brilliant post: https://blog.hiler.eu/win32-the-only-stable-abi/

Speaking of FreeCell, a couple weeks ago I was visiting my 95yr-old grandmother and noticed she still plays oldschool FreeCell, specifically a variant that's really hard to track down now called FreeCell Pro [https://cards.fandom.com/wiki/FreeCell_Pro]

It inspired a weekend project. I always liked that you could swap the card backs in OG FreeCell and play with different "themed" decks, so I vibecoded something a little more modern. I got carried away and added a roguelite mode too (yeah I know how "Roguelite FreeCell" sounds). Anyway, it's free to play on the web, no ads: [https://freecellworlds.com/]

> At the time of this post, that’s a 33 years and 8 months old application,

Pointing this out without a trigger warning is just rude ;-)

Some of us are older than we think, yo.

Along these lines, I'm always amused with the videos (e.g. https://www.youtube.com/watch?v=C8CIhCTVyqQ) showing you can update a [virtual] device from Windows 3.1 to Windows 11.

In 2026 does it still make sense to build new Windows app using Win32 API? I was building a simple image viewer similar to QuickLook on Mac using Win32. I found it's very responsive. The code is less readable compared to React. For me Win32 is a good option if the UI state machine is simple enough.

I often think old GUIs have a nice, functional look to them. This one is no exception. I notice (what I assume is) the shuffle toggle looks unfamiliar. This is from way back before that UI became a convention! I see the repeat icon has stuck around. So interesting!

I remember having installed Win32s package to our Windows for Workgroups 3.11 machines at Osmangazi University in 1995. The idea was that Windows, as a 16-bit operating system, could run a subset of Win32 apps that were compatible with the Win32s API surface. However, the release of Windows 95 had almost immediately made it obsolete. I'm sure it was useful in certain scenarios, but our only win was Freecell. :)

> That is because, duh, my computer doesn’t have a CD-ROM drive. But you can use a small DLL (cdemu.dll) to emulate one with some fake audio data and actually get it to play audio

This makes me curious to know if CDPLAYER.EXE would still work (unmodified, without extra DLLs) with a real CD-ROM drive if you ran it on a Windows 11 machine with one installed.

"Can you believe it... Reversi" reminded me of the Steve Ballmer ad for Windows 1.0: https://www.youtube.com/watch?v=DgJS2tQPGKQ

EasyToon (from 1998, I believe, built for Windows 95) runs on Windows 11. One of my favorite pieces of software.

It's a thing for making little black and white animations. (With GIF export.)

It was popular in the early 2000s and there was a subculture around it on animation forums.

English version (hey, still online!):

https://www.superfundungeonrun.com/easytoon/

Original version (Japanese, w/ screenshots):

https://web.archive.org/web/20020111185602/http://www.radium...

There's also a forked version on a French website (also available in English) with some extra features. But I like to keep it simple :)

https://www.flat2d.com/easytoon.html

Microsoft is known for making Windows run older programs. Apple not so much.

You don't even have to find old binaries. The ODBC manager is still shipped with Win11 and has Win3.0 / NT3.5 dialogs with 16-color icons.

There's probably an old X11 app from the 1980s that could be executed through xwayland somewhere.

> And although using otvdm does feel like cheating, I thought it was cool enough to include in this post.

Honestly, if NTVDM was part of Windows then it seems fair to use it, even 3rd party clones.

Wrote a few small utilities in Win32 in the early 90s; still use them today unmodified, but most recently in WINE. I have some slightly older DOS utilities that are also quite usable.

Very nostalgic. I think UI today is too simplied, but I can't stop making kind of that, because many user are not a member of Hacker News.

If you tried this on Linux desktops you wouldn't get far

Here I was thinking it would have been Kedit…

Does visual studio still package the Spy++ exe that looks like its from the early 90's

That's a year before the first PowerPC Mac even shipped.

kudos to microsoft for enabling 40+ years of API support. Most companies are ending support after less than 10 years. some even a few years ( like those Nest thermostats getting killed )

Can you imagine the maze of a diagram that enables these old APIs to draw to the screen and render controls properly still?

> Sadly, Windows 11 can’t run 16-bit Windows programs by itself, because 64-bit Windows has no NTVDM, so we’re going to have to find something from the early NT era.

I remember a recent-ish post on here that really, I mean really, dived deep into this whole thing. It turns out that it was mostly a lack of willpower or maybe political that stopped Windows 64bit running 16 bit apps.

Somewhere in the kernel, with some obscure mechanism there is support for some kind of emulation that if implemented would allow it to run NTVDM and therefore these 16 bit apps.

The author of the post even had some kind of proof of concept of running a 16 bit DOS app directly under Windows 64 bit with this.

The details are blurry, but I believe that that had the Windows team really wanted to this emulation could have been built in and totally seamless.

I got the impression that this was actually a fairly new finding which is why I suppose no one has tried it.

Related: "Chain of Fools : Upgrading through every version of windows (HQ)" (2011), they upgrade Windows 1 through to Windows 7, and demonstrate Doom II and Monkey Island working still at the end. Would be interesting to extend it to Windows 11.

https://www.youtube.com/watch?v=vPnehDhGa14

I'm imagining a future where Microsoft's Copilot pops up in the corner, Clippy style, and gives you a message like, "Hey, I noticed you're running an app that looks like it was developed when Windows Vista was new. Want me to freshen that up for you?" Then it runs a decomp/recomp process that updates the app at the binary machine code level so that it looks and feels like a modern app without any translation layers or weird bugs. No more user complaints about Windows having an inconsistent GUI.

Interesting.

At one tine, Slackware Linux would not recompile binaries unless the program was patched. So there was a time you could find rather old binaries on Slackware, and maybe still on other distros.

I wonder what the oldest unchanged source/program running on Linux or BSD ? My vote goes to cat(1) :)

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