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Oldest GUI application that still runs on Windows 11

https://blog.enlyth.com/posts/oldest-windows-gui-app-win-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.

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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.
Android used to have a dedicated menu key that would always bring up a menu. It was removed to chase Apple's 100% screen design.
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Just got nostalgic about the 4 hardware buttons on my Sony Xperia Play: back-home-context(option)-search.

Still the best navigable phone I had when coupled with the Nova Launcher gestures.

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I am fairly bothered about that but the one that really gets to me is the inconsistency of user interfaces across applications.

This precisely coincides with the web developers being allowed to wrap stuff into "apps" in Electron and the like.

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So do I, but I don't think I'd blame mobile-first designs, and instead place the blame on Microsoft sucking at making decisions, sucking at design, and sucking at mobile. Every bad Windows UI has, imo, been the result of trying to be cool and likeable by dying their hair a different colour to get some attention and getting ahead of or catching up with Apple who was playing a different game the whole time.

Apple meanwhile has made some notable mistakes, but when they do, it's usually a thorough bad bet that's just missed the mark, but if they do, it's all throughout their OS in every corner. Even with their recent Liquid glass blunder, they're not really putting a veneer that looks like wood over a rotting corpse of a house, they're just picking bad materials to update an otherwise decent layout. Microsoft's whole track consumer UI/product record imo is trying and failing to bet small but intrusively on ideas that don't work, aren't cool, and have no longevity. You see it as soon as you open the control panel that still looks like the 90s; it's this uncomfortable amalgam of failed tepid temporary marketing pitches by some department that make no sense

Windows 95 was the last release that had serious user testing in controlled environments. (They were also cribbing lots of notes from NeXT, which helped.)

Something fundamentally switched around 1998-2002 in how interface design was viewed and approached. I started my career in software as a design summer intern at a company that made a Windows “groupware” application in 1997. They took pride in following the platform’s guidelines and actually testing their designs with real users being videotaped trying to use it. The company’s UI design department was tiny, but employed both an industrial designer and a cognitive scientist.

Five years later, everybody I met in UI design was a graphic designer who was drawing glossy website mockups in Photoshop. The elder lore of science-based UI design was completely lost when Web 2.0 happened and app designs became vibes-based. Even Apple couldn’t resist the tide. (Indeed Steve Jobs’s return to Apple in 1997 was a major contributor because he had developed a taste for user-hostile skeuomorphism like the brushed metal QuickTime Player.)

I don't think that's true.

I was at Microsoft when they user-tested Windows 7 to death. Including installing eye tracking software during sessions so you could monitor where the user was looking at on the screen.

That data was in part used to justify the changes made in 8: "Users only click on the start menu 0.1% of the time and when they do they focus on a narrow portion of the screen."

A couple of the UX people who worked on Win8 told me that some of the UX study results were faked to give the desired results that justified the new Win8 design changes.

Def the sort of stories you hear at at a bar after work.

Skeumorphism is the opposite of user hostile. Flat design. Now THAT is user hostile.
You’re not wrong that they aren’t directly correlated. I can see the argument though that making Notes look exactly like a yellow legal pad was not an automatic gain for usability compared to say, wordpad.exe with its super simple toolbar that showed you every option.

I think a fair take is that going full skeuomorphic may take some options off the table for you because they would conflict too much with the metaphor you’re leaning hard into.

I’m still 100% Team Forstall though, considering the massive violence that ios7 and its copycats have wrought on usability.

Some skeuomorphism is user-friendly, like buttons that animate like they're clicked when pressed down. Other skeuomorphism was user-hostile, like the various mouse-only interfaces where everything had to be dragged around to work.
Skeumorphism where "things look like real things" can be fine. Complete skeumorphism where "things act like real things" is user hostile.

The poster boy for that is the old QuickTime Player, which had a volume wheel and a drawer for shortcuts. https://www.johnforde.com/teaching/shame/qtime.htm

The war on scroll bars has gotten pretty senseless.
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The Desktop GUI was perfected with NeXTStep in 1990. Though some might say Smalltalk in 1984 (modulo some nice artwork and colours).

We could even have unified desktop.mobile codebases, with different GUI layouts. 280 North's objective-J/Cappuccino proved this.

IDK what we're even doing anymore.

The early Mac made huge functional improvements over the Smalltalk GUI, improvements still used today.
> IDK what we're even doing anymore.

I would say people are just disagreeing with you that the situation is actually so black and white.

Although I started with 98, I think Vista / 7 was the peak. It was user friendly enough for newbies but didn't sacrifice advanced controls. Just organized them better to bring focus to the more used parts.
In terms of aesthetic, I love Windows 7-era Aero glass design (and to a lesser extent, Vista), but I also love the classic Windows 9x/2000 look. If I had to choose between the two, I'd go with Aero simply because of the start menu search bar.
In both Windows 7 and Vista you could change the theme engine to Windows Classic, which gave you the Windows 9x/2000 look AND the start menu search bar.
Exactly. Windows 7 plus the windows 2000 "classic" option was pretty awesome.

Win10 LTSC with the right options and limiting search to local only is pretty good also though. Insanely snappy on even crap systems (with really any SSD)

Maybe on the OS side. However, Vista coincided with the release of Office 2007. That release of Office introduced the dreaded Ribbon, which made functions much harder to find.
I actually like Ribbon and I disagree. It made functions easier to find, for people who didn't have a muscle memory of those functions. It actually taught them how to use the program and exposed conditional menus like picture options better than the toolbars that appear and disappear.

Of course people who got used to traversing 3-level menus got annoyed but they still have all the same keyboard shortcuts. However, spending enough time, you also get used to Ribbon and it usually requires fewer clicks not more.

I still find a tastefully done Ribbon is better than a menu and a toolbar combination. The problem is, not everybody has put the same effort that Microsoft did which created monstrosities like Solidworks Ribbon.

I loved Windows Aero and the flip 3D view - the latter mostly because it looked so cool for that time!
Oh you mean "ripping off compiz"?
I just learned that X Window System came out a year before the first Windows release. Interesting. Thanks for pointing out the compiz ripoff. It spurred me to look up the original release dates.
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I used the Zune theme for windows XP which I really liked. I dreaded Vista because it was just a resource eater with all the effects turned on.

https://www.softpedia.com/get/Desktop-Enhancements/Themes/Mi...

The zune theme is great, now on my XP machines i use a mod of the MCE theme called Royale Noir which is my absolute favorite.

https://images.sftcdn.net/images/t_optimized,f_auto/p/5c889a...

> we lost the menu bar and replaced it with "mobile first" designs

What does this mean? I use lots of apps that still have a menu bar.

Some apps eschew it, like browsers, but not because they are “mobile first”, but because they are trying to maximize screen space.

> Some apps eschew it, like browsers, but not because they are “mobile first”, but because they are trying to maximize screen space.

I don't think this is true. If anything, we see more oversized buttons and empty space nowadays. It's as if developers forgot that PC users have keyboards and mice. Remember, display resolutions and monitors were a lot smaller back then, and making space count was arguably more important 20 years ago than it is today.

Smaller screen also means your menu bar has to be larger relative to the total screen size to be readable though. Assuming something like the standard going from 15" or 17" CRT to 24" LCD
Two things can both be true. An app can create more space around controls and get rid of the menu bar to save space.

The space also really has nothing to do with “mobile first”. It’s for touch screens (and also modern aesthetic that avoids crowded controls).

To be clear, I am not saying that all apps are optimizing for saving screen space. I was specifically talking about browsers, which are broadly optimized to give as much area as possible to the content.

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> but because they are trying to maximize screen space

If that was the case they wouldn't put giant margins around every UI element and dead space everywhere.

My browser doesn’t have a bunch of dead space. No footer. One line for controls. Tabs have been collapsed into the title bar.
I loathe mobile first design, seems to me it's "mobile matters, on other devices just deal with it.".

The Wells Fargo website screams this for me - it used to be dense and packed with info, now it's got large elements and wasted space.

> they are trying to maximize screen space.

Ironic to say on hackernews which shows massive whitespace in the margins-- and if I try to widen my tab sidebar it actually indents the margin rather than eating into it.

One can look across the computing space as a whole and see that, it is surely not the case that we're "maximizing screen space".

Totally agree. But this does not take away from his point that maximizing screen space is the motivation in Firefox. In fact, all you have done is demonstrate why they are driven to do so.
Maximized screen space doesn't really benefit this site.

The key element missing from this thread is that the Internet going from a text based to a multi-media (and increasingly video-centric) experience.

A lot of Internet users, at this point, do as much reading on their phone or laptop as I do reading on my TV (almost none).

You think Hacker News’ design is new? It’s looked exactly the same since I started using it over a decade ago.
> I use lots

Oh really? I, sadly, use nearly none. Open on my desktop right now: Slack, Outlook, Zoom, Windows Terminal, Edge, Claude, Obsidian, whatever the Windows image viewer is called, Cursor, and VS Code.

Only the last 2 have menu bars. And I can’t be certain that I didn’t dig through the preferences of one or both of them when I first installed them to tell them to knock off the bullshit and give me back the menus. Once in a while, there is an option buried somewhere like that.

In fairness I did not do a full inventory of all the apps I use. I see Word and VS Code. It may be less than I thought if I inventoried every app I regularly use.

I see some have gone the “browser” direction with tabs folded into the title bar and the menu bar dropped. Windows Terminal, File Explorer, and Notepad are all that style now.

Edit: Actually Notepad has the tabs in the titlebar thing but retained the menu bar and folded it into the command bar.

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Working directly with C API in Windows has not been a thing since Vista, as COM took the main role for API delivery.

The Windows SDK samples like Hilo make use of C++ with COM.

How can it be related to perfection to permanently waste a strip of space you rarely (and in some apps never) use?
Wasn't that Windows 8 ?
Windows95 still had failures of UI design, and those weren't fixed until XP.
The Menu + quick access bar was good for developers but terrible for users, at least compared to the ribbon.

Ribbon is absolutely an improvement for users but is more work for the XML layout and learning how to organize it.

I'm rather convinced that Ribbon is still the best way to organize quick actions, show their shortcuts (Alt to see keyboard shortcuts), and also have enough text to describe all the buttons. But it'd be nice if it were easier to make good Ribbons.

Menu was braindead easy, albeit through ancient process of .rc files and whatnot

The alternative to ribbon is not menu+ quick access, it was easily customizable toolbars where you can simply drag and drop only the buttons you need in the toolbars you need at a fraction of screen space that the ribbon wastes. And no user is ever exposed to that XML garbage only a dev could love
Menubars/toolbars were not n00b-friendly but great for anyone that used a computer for technical reasons.

Old Photoshop, any CAD software, Excel. Smaller buttons and more of them is a steeper learning curve but results in far superior day-to-day usability. You can still hold down [Alt] and see hotkeys, that wasn't unique to the Ribbon UI.

it's all very much an example of the "Look at what they need to mimic a fraction of our power" meme.

I'm just not sure why it has to be one or the other. Look at NeXTStep. They had a menu bar (or I guess a menu panel) and a ribbon, although that term didn't exist yet, and it was definitely not 100% there yet.
I think it's the other way around. Well organised menus can help users discover what functions are available at quick glance without having to hover each icons with the mouse to know what they do. For power users, the ribbons mean you can click directly on the function you need without having to click through menus and sub-menus.
Menus from Win95 are uniform. All buttons took up one row and a full width of the submenu. (Even if you don't have a shortcut key assigned, the space is taken up and wasted)

It's well acknowledged that modern designers and users benefit from large vs small, and other varying styles of organization.

Menus only had top menus vs submenu vs sub-sub-menu (and so forth). Yes a good menu is useful but...

A ribbon offers many more tradeoffs. It's harder to design a good ribbon, but the best ribbons are always better than even the best menu. The important features will be physically larger with more text and space. The less important or niche features might just be an icon with tooltip, possibly hidden behind a subcategory of the ribbon.

In theory, you can use the modern Ribbon to make old school menus. But why bother? If you made the switch to that XML design language, you might as well take all the benefits of the Ribbon

Or hell, if you like old school menus, you can still make them today. Those .RC editors still work in modern Windows 11. But give it a shot and you'll see how restrictive and bulky old school menus are in practice.

> The desktop UI was perfected around the time of Windows 95

There’s no need to be hyperbolic or blinded by nostalgia. Yes, user interfaces have suffered several setbacks in the years since, but even if we concede every change was for the worse (they weren’t) it was by no means “perfected” and there was still plenty of area for improvement.

> The desktop UI was perfected around the time of Windows 95 and has gotten worse with every iteration since then.

Well that can't be entirely true, the desktop experience on Windows 10 improved on Windows 8 by leaps and bounds.

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95 feels kinda backwards tbh but 98SE/2000 is outrageously modern. A lot of the windows admin tools are unchanged from 2000 apart from the icons. I really think if you could run a modern browser on 2000 it could be a daily driver for most people
As computers, and smartphones got more popular, the audience got larger and the use scenarios got more and more distant from professional use. Dedicated professionals, like software engineers and stock brokers still prefer CLI and Bloomberg terminal even today. Ordinary office workers late 90s and early 00s window-based interfaces (the ones you're talking about). But smartphone users who just want to play their free games and scroll through facebook actually prefer the mobile-first UIs.

If you see this UI transition through the same lense as CLI-GUI one, a lot of things become more clear, in my opinion.

I agree with you generally but I don't think desktop UI is remotely close to perfected. Unless you mean the desktop as a skeumorphic concept than maybe.

I think we've actually completely stagnate on the human interaction side of OSes and only emacs has made any progress and then only for those willing to put the work in, not as a vanilla user ui.

i agree. i love the 120hz responsiveness of the UI. how fast the app loads, the buttons click. No lazy loading , placeholders, layout re-renders. Open the task manager: half a meg ram used.

Insanely great performance.

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.

Makes me wonder if forking Wine to have a "Legacy Windows" compatibility layer... for... modern windows would be worth half a damn.
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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 think the point made here is that the application runs as if it were a modern application, even though the OS is completely unrecognizable when compared to the OS it was written for. There are other ways to run old applications on modern hardware with modern OSs, which the author would consider cheating for the purpose of TFA. Heck, I can run ancient DOS and gaming console applications on my phone if I wanted to.
a better example would be whether you could put a train from 1845 on a modern track, or fire a musketball from an M16
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I guess this is one of those proverbial “I had to create an account to comment” messages:

https://m.youtube.com/watch?v=pQHX-SjgQvQ

https://xkcd.com/1909/

It is amazing, though. Wintel is basically a Matryoshka doll (Russian nesting dolls), where each version contains all the previous versions. (Just look at how a PC boots up!)

The dedication to compatibility is commendable, and you don't really see it on the other OS's. On that note, this is one of my favorite articles:

Win32 is the only stable ABI on Linux

https://blog.hiler.eu/win32-the-only-stable-abi/

I think that's very funny. Speaking of which, EasyToon also runs in WINE, of course :)

https://news.ycombinator.com/item?id=50250809

Give it a few centuries of evolution and maybe we'll get there
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/]

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> 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.

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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.
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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!
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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. :)
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> 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.

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"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.
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> 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.

Yeah I was kind of on the fence with this, but since the last version of Windows that shipped with NTVDM was Windows 10 32bit, and Windows 11 doesn't have a 32bit edition, I decided that using 3rd party tools would be cheating

I was aiming for something you could double click on vanilla Windows and would just work out of the box

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.

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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

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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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