Windows UI evolution: Clicking an unassociated file

https://movq.de/blog/postings/2026-06-20/0/POSTING-en.html

by jandeboevrie • 1 month ago

142 112 1 month ago

shevy-java• 1 month ago

Can it really be called evolution? That sort of implies an improvement.

Interestingly enough, the default GTK file chooser also sucks. I notice this nowadays because I broke something in my setup but I don't know what, and the default file chooser does not remember anything I do. Prior to that I found out that for opening files via the browser, I need to have e. g. xdg-desktop-portal-gtk running. Well, my browser never told me that; it just silently failed to download anything, I could not choose any local file for file upload. I only found out eventually, but when I found out, the fix was easy, but still, the question is why such things break silently. This is simply incredibly poor engineering and design, and that happens on linux too. That way they'll never achieve linux desktop of the year. The decision makers here are just horribly bad at designing anything. The whole GTK team fell victim to this, now that it is a GNOMEy toolkit only.

When we ever get one-toolkit-that-fixes-everything (well ...), hopefully they are really allowing only mega-smart people who can think objectively and try to IMPROVE things rather than regress or take away functionality willy-nilly style (as the GNOMEy devs do).

wolfi1• 1 month ago

evolution need not necessarily be an improvement, foe example mammals have a blind spot in their eyes because of the optic nerve, octopuses don't have a blind spot. but octopuses were before mammals

adrian_b• 1 month ago

Biological evolution has indeed lead much more frequently to simplified, streamlined structures good for a single purpose, which had evolved from more complex and more versatile structures, than to more complex structures that had evolved from simple structures.

The latter kind of evolution events, while very rare, had a greater importance by being the origin of various kinds of very successful living beings.

Your example shows that because evolution proceeds through random search through the space of solutions, inside the neighborhoods of the starting point, followed by the choice of the best solution among the candidates, it frequently fails to find a global optimum, but it remains stuck on a local optimum.

However, octopuses were not before mammals. Both octopuses and mammals had appeared around the middle of the Mesozoic, but this is not really relevant for their eyes, which already existed in much older ancestors, hundreds of millions of years earlier.

Cephalopods and vertebrates with complex eyes already existed during the Ordovician. Chordates with complex eyes might have already existed quite early during the Cambrian, most likely before the separation between cephalopods and other mollusks, at a time when mollusks must have had only simple eyes that could detect light and perhaps the shape of shadows, but which could not form images.

When cephalopods separated from the other mollusks, they did this by evolving the ability to swim, instead of being forced to crawl on the bottom like most mollusks. (Swimming was achieved by filling their shell with a gas, which made it buoyant, while the other mollusks were held on the bottom by the weight of the shell.)

Chordates have also separated from their ancestors by evolving the ability to be fast swimmers (the elastic and incompressible dorsal chord reduced the energetic cost of anguilliform swimming in comparison with that for worm-like bodies that need to contract a muscular layer in order to prevent the shortening of the body when it is flexed).

This is likely to not be a coincidence, so the evolution of complex eyes in chordates and cephalopods is likely to be linked with the evolution of swimming in both groups, which made important the detection of objects located in various directions, while for a bottom crawler it could have been sufficient to sense when a shadow appeared due to something coming above it.

fifticon2• 1 month ago

I concur, I would say evolution is more like "adaption" than improvement.

inigyou10• 1 month ago

at this point GNOME is a joke. I'm not sure KDE is always better but at least KDE is clearly trying. btw Wayland is also a project of the GNOME team and almost everyone is using the KDE extensions to it to make it suck less.

fifticon2• 1 month ago

I'm not sure you can blame the GNOME people for not trying. Personally, I feel like they are actively trying to make it worse, ie they are not passive. Their approach to file system dialogs (open file/folder, save file), was what got me to finally realize, that I must necessarily prefer KDE, because I must necessarily prefer anything that is not GNOME. Now if I could only figure out how to stop KDE from opening file dialogs ALWAYS BEHIND ALL OTHER WINDOWS, that would be even better, but you can't have it all..

One day, when I die, and go to heaven or hell, when I arrive, my first question to the ones receiving me, will be "Finally, tell me - is there ANY possible way to navigate upwards to the parent folder, in GNOME?"

lunar_rover2• 1 month ago

Most works GNOME did are somewhat invisible to users. GNOME is the main driving force behind immutable OS and containerised sandboxed apps, both are intended to make the OS maintain itself and simplify software management to single/zero click.

Valve adopted them afterwards and now everyone in the KDE team wants to join the ride.

edg50002• 1 month ago

I daily drive GNOME on Ubuntu 22 on a daily basis and its UX is the favorite of all the UIs I've ever used, and I've used classic mac, OS X, all windows versions, xfce, kde and a trillion programs. And both android and ios devicess, both from early versions onto recent.

And GNOME really shines here. I'm on X11 though. Wayland lagged my mouse when I tried it years back, so I gave up on Wayland. Maybe they've fixed the lag spikes.

janci2• 1 month ago

I never understood why file open/save dialog is a separate thing. I want to use my file manager to open and save files!

formerly_proven2• 1 month ago

Win32 has good news for you!

Kwpolska• 1 month ago

You need a separate UI to handle things like entering the file name and filtering for appropriate files. Windows was designed so that the same file browser component is used in the Explorer and in open/save dialogs (but with Windows 7-era UI), but on Linux, which file manager should GTK use? GTK sometimes likes to pretend it’s separate from GNOME.

edoloughlin• 1 month ago

One thing that drives me nuts every time I save a new file or 'save as'. File chooser appears and I automatically start typing to enter/change the filename. But the filter input always gets focus and now I'm filtering the list of visible files instead of naming my file...

(Yes, I know I could try to submit a PR but I don't have the energy to figure out the Gnome governance process.)

bombela2• 1 month ago

plus the filter search is very slow. plus the async race conditions if you click or keyboard enter too quickly.

kenjackson• 1 month ago

How is this not an improvement?

reddalo3• 1 month ago

I think Windows 9x was peak Windows.

Everything is clear, you know what's a button and what's not. Information density is also high, which is a good thing on a computer screen.

But the main thing is that Windows 9x felt responsive. The Windows widgets felt solid and performant, while "modern" UWP apps feel clunky and prone to breakage. And don't even get me started on Electron.

Edit. See OP's previous article here, he managed to capture what I was trying to say in more details, with nice screenshots: https://movq.de/blog/postings/2026-06-16/0/POSTING-en.html

xuhu• 1 month ago

Products have to change in a visible way so people know they're new.

Aldipower• 1 month ago

Same with running shoes, and they get worse too..

flohofwoe• 1 month ago

This is because back in the 90s GUI development was still driven by hard research, not by "emotions" (e.g. actually sitting very diverse groups of people in front of computers, asking them to perform specific tasks and then analysing where exactly they got stuck or became confused).

IIRC this golden era of GUI research fell apart once people started to call themselves "UX designers".

pegasus2• 1 month ago

Everything is clear, you know what's a button and what's not. Information density is also high, which is a good thing on a computer screen.

I would say information density was too high. All those always-on indicators: 3D scrollbars, buttons, etc. create a very busy picture. Today's interfaces are much cleaner which comes at a price of less information and hence, more ambiguity, but I for would rather pay that price than go back.

One problem I see is that while the UI itself has been simplified, incidental complexity has crept in other ways. Most importantly, the OSes themselves as software systems have clearly grown ponderous and unwieldy so that today they are more bugs and more of those bugs can be subtle and surprising. Also, there is less uniformity in UX across apps (and UI frameworks).

vjvjvjvjghv• 1 month ago

"Today's interfaces are much cleaner which comes at a price of less information and hence, more ambiguity, but I for would rather pay that price than go back."

If you take today's interfaces to an extreme, you would get a white sheet. Very clean, but unusable. I wouldn't call interfaces "clean" where users increasingly have trouble figuring out what's clickable, how to scroll, move or resize a window.

chmod775• 1 month ago

I would say information density was too high. All those always-on indicators: 3D scrollbars, buttons, etc. create a very busy picture.

Have you been in nature recently? We've evolved to deal with very busy pictures and parse relevant information from them.

New UIs often don't have relevant information - like what is clickable or scrollable - and that's a problem.

It used to be that grandpa couldn't find a button with his poor eyesight, since everything was cramped and too tiny on the small screens we used to have.

Nowadays the clickable label is hidden behind a tiny hamburger menu that you can't tell apart from a mere stylistic flourish on the massive screens we keep mostly empty. Now neither of us can find the button.

That's progress? Every time I open an old application I breathe a sigh of relief because I can feel the cognitive load decreasing. Not having to put myself in the headspace of the designer to figure out what random geometric shape happens to be interactive is like taking a vacation.

inigyou10• 1 month ago

I think this is a consequence of cultural changes in the last decades. It used to be normal to be able to open a settings window, or any other window, and read it, top to bottom or in any other order, and then you'd know what was there and where it was and which parts you don't care about.

I think it's much better than hidden features practically. But now we've developed this cultural aversion to complex-looking things. Probably started when the iPhone came out with just a flat screen and a button.

hulitu7• 1 month ago

Today's interfaces are much cleaner

They can do better. Eliminate any distinction between elements and between background and foreground. Cleanliness at its best. Computer are toys anyway, nobody "works" on them anymore. /s

jameshart3• 1 month ago

Windows 9x did not feel ‘performant’. This is a false memory people seem to have.

Spinning rust hard drives were slow. It took ages to launch a program - loading screens typically had time to display a progress bar and a series of notes about what they were up to - ‘loading extensions’, ‘reticulating splines’, etc. Word would stall whenever it was autosaving. Carrying out an operation like spell checking or doing a find across a whole document or getting a word count took time.

Remember windows used to have an hourglass cursor? You used to have to watch that thing flip and empty multiple times when doing things like emptying the recycle bin.

Windows 9x was typically not running on a permanently networked computer. The computer wasn’t running a bunch of background network tasks like checking for updates or polling your email - generally it was just being slow because it could barely cope with running more than one program at once.

j1elo• 1 month ago

Thanks for reviving the reality of it. I saw the hourglass icon so many times, that I am able to picture all of its frames in my mind. Windows 9x might have been close to peak UI design (for me I'd say Windows 2000 is the sweet spot, and I always configured "Classic Style" on Windows XP and 7), but 95/98 was not responsive. And that's when it wasn't crashing.

SanjayMehta3• 1 month ago

Word 2.0 forever made me distrust Microsoft with an error: "File too large to save."

It was on a 20Mb hard drive, and the file was small enough to fit on a 1.44Mb floppy.

Turns out it was an obscure defect in Word: if you had quick save on, and the last page had a diagram or image, it would choke. Quick save or fast save - I forget what it was called. This would append deltas to your file, I think.

exitb• 1 month ago

I have a running Windows 98 PC with P3 550MHz and SSD connected via IDE adapter. The drive is a bit out of place, but it’s legitimately the fastest booting, most responsive computer in my house. Its only speed issue is that it can really do just one thing. Any heavy task (including large file/network operations, apparently) will render the system almost unresponsive until it’s finished.

bananaflag• 1 month ago

This is a false memory people seem to have.

I have no idea where that false memory is coming from, I also remember being utterly frustrated by Windows 98 on 450 MHz with 64 MB RAM. The only systems ever which felt performant to me are modern minimalist Linux on modern hardware.

badsectoracula• 1 month ago

For a long time i had a small Pentium III PC (released in 2000, though the hardware inside wasn't the best you could get at the time as it was meant to be compact instead of performant - it was in an almost pizzabox sized case) running Windows 98 for retro games and software (though mainly games). At some point i installed Visual Studio 6 to it too - and IME it launched instantly[0].

In general everything ran fast... except stuff that had to do a lot of disk access, obviously (i.e. installers and such). But i never though that the system didn't feel responsive.

Also many modern programs have splash screens too. E.g. have you tried to launch Gimp or Krita recently? Or Eclipse? "Heavy" applications never stopped having those.

Of course computers are much faster now, nobody is saying otherwise. What people are saying is that it often doesn't feel so. If my Pentium III can open Visual Studio 6 faster than my 3700X can open Calculator, then yes, things do feel more performant on the Pentium III running Windows 98 even if the modern machine is much faster.

[0] https://www.youtube.com/watch?v=h79Bt7h5ceo

inigyou10• 1 month ago

Windows 9x achieved performance only a small factor slower than what we've got today on 1000x faster hardware.

VS6 was mentioned in a sibling comment - Casey Muratori's project loading and watch window stories come to mind. He had a video, which I can't find any more, showing him loading an identical project, compiling, starting the debugger, and watching a variable while single-stepping in VS6 on Windows 95 on Windows 95-era hardware, and the same on Windows 10 on Windows 10-era hardware. Guess which one was faster. It wasn't Windows 10.

Yes when we talk about the past there's an element of nostalgia-tinted glasses but there's also an element that stuff is just fucking worse now, and for no good reason. (I blame landlords - think about it. The whole economy is being pushed to do more with less because the value extraction related to land keeps increasing.)

Discord today does not load more quickly than MSN Messenger used to.

vitally3643• 1 month ago

Windows itself was snappy and when it was slow it was because the machine itself was slow. This was communicated to the user by the machine making a hell of a racket doing machine things.

Windows was fast because the machine was slow. Now we're in a situation where Windows is slow in spite of running on a machine that outclasses every computer in the world combined 30 years ago.

freeone3000• 1 month ago

Put an SSD and a modern emulation behind Windows 98 and it flies. You’re excusing inefficient software because it was paired with improved hardware.

api• 1 month ago

This is true but also false.

It’s true that things could be slow on those old machines, especially when it had to hit disk. It’s true that things were often single threaded and would stall.

But what’s also true is that this old code was orders of magnitude more efficient. Put that code on even a modest machine from today with an SSD, even a Raspberry Pi, and it would scream. Everything would be instantaneous.

Some of the reasons for this degradation are unavoidable, like high DPI displays and feature depth, but a lot of it is just bloat on top of bloat on top of bloat.

hulitu7• 1 month ago

It took ages to launch a program - loading screens typically had time to display a progress bar and a series of notes about what they were up to - ‘loading extensions’, ‘reticulating splines’, etc.

Just like today, without the progress bars. And some "apps" even cheating by being preloaded in memory.

marcosdumay• 1 month ago

By 2000, Windows 98 felt extremely performant. By 1995, Windows 95 was the bloated thing trying to replace Windows 3.11 that would take ages to boot and needed minutes to respond to a click at random.

rkagerer2• 1 month ago

With those slower drives, programmers tended to be more careful about not wasting those preciously expensive I/O's - they had to put more care into architecture, often resulting in more optimized, efficient code. And since lags were expected, they handled waits more elegantly - hence the hourglasses and such. This immediate feedback even when there was a delay is what made the experience feel more responsive.

Modern apps that ship with browser engines just to show some UI are hugely bloated by comparison.

You also didn't have dozens of different telemetry, update, crash collection etc. services constantly running in the background eating up resources and I/O's. Go into Event Viewer, Services, and Scheduled Tasks on a pre-Win7 era workstation and you see how much less crowded it is.

raincole• 1 month ago

It's crazy that people keep talking how fast the computers were. They weren't. It's amazing that they could work with so little hardware resource compared to what we have now, but old PCs were not "snappy" in any way.

mock-possum• 1 month ago

Remember windows used to have an hourglass cursor?

God thank you, yes, I actually do think that most have actually forgotten what UI was like back then. Rose tinted glasses are such a weak point for people.

EnnEmmEss• 1 month ago

Was reminded of this article when I read what you said: https://brooker.co.za/blog/2026/06/19/waiting.html

I have an ancient Windows 98 computer which I used to use at my grandparents' home until a few years ago. All the problems you mentioned did exist. However, the machine still felt more responsive than today's laptops. Something being objectively slow is very different from it feeling slow when you use it. As an example, I never had Word autosave turned on. It was always explicit (even if this meant I'd usually lose what I was working on when the computer lost power)

pjmlp2• 1 month ago

Nah, that goes to either Windows 2000 or Windows 7.

SanjayMehta3• 1 month ago

Windows 2000 Professional was peak Windows for me. Skipped XP etc thanks to mac. Then 7 for a while.

DrBazza• 1 month ago

This is the correct answer. Win2k was probably the most solid and cruft-free release that they did.

Then the enshittification started with Window XP, jelly-mold/curved glass buttons, activation, and .NET everywhere, followed by the disaster that was Vista.

They released Windows 7, and somehow then decided, yet again, to screw things up with Windows 8 because 'mobile'.

GeekyBear2• 1 month ago

Windows 2000 was the last version of the Windows NT lineage with Dave Cutler in charge of everything.

His no-nonsense attitude towards fixing known bugs was sorely missed in later versions as Windows quality began its decline.

narag• 1 month ago

I think Windows 9x was peak Windows.

I'd choose XP instead. People disputing the performance maybe should consider the hardware at that time. Real problem with 9x was low-level stability. Juggling with compatibility was difficult, file access comes to mind, it was a kludge. It was possible but hard to maintain the system in a sensible state.

XP was the first to bring NT architecture to desktop. It was a huge success. Many despised the colorful UI, I actually like it. They started moving things around, but annoyances were fixable. Microsoft has adopted more of a "my way or the highway" attitude since.

reddalo3• 1 month ago

Yes, maybe XP was the sweet spot between ease of use and ability to revert back to a "classic" Windows interface.

It also had many multimedia features for burning CDs, editing videos, etc..

bee_rider2• 1 month ago

XP was quite ugly though. 98 or whatever was the best looking, but 7 was probably best overall (because they’d at least somewhat improved the UI and the system was generally more stable and modern).

(FWIW I mostly switched to Linux after XP so this isn’t nostalgia).

BirAdam3• 1 month ago

People also forget… XP had more than the one tonka-toy theme from Frog Design. There were several themes. Some appealed to my visual tastes, some didn’t… but I do think they were well designed, which is more than I can say for most UI design today.

afzalive• 1 month ago

Wasn't 2000 the first NT architecture on desktop?

2000 is, by far, my favourite Windows OS.

linguae• 1 month ago

XP also introduced activation, which is one of the reasons I prefer Windows 2000 to XP.

hulitu7• 1 month ago

XP was the first to bring NT architecture to desktop

That was Win2k (DirectX). XP was full of bugs and holes before SP2.

prmoustache• 1 month ago

I'd replace 9x by windows 2000. It was the only decent windows. 9x were BSOD crashfest, 2000 was stable as NT but without the enshittification of XP (ugly default themes, stuff above calling internet services with zero value).

I think what you describe as responsive are 2 things:

1. absence of animations. I don't know about windows but on linux DE you can disable them, it feels snappier but more raw and I think most people still prefer the animations.

2. Visual and audio clues. Back in the days we were on spinning disks so anytime you'd click on somethimg you would hear the disk moaning in pain and see that disk led blinking. You knew that something was happening, even if it took a long time. When SSD were introduced, everything became instant and silent for a few years, it was pure bliss. Then over the last decade apps continued growing and growing in size and as fast as they were SSDs and NVME started not feeling that fast because so much stuff had to be loaded into memory. Nowadays many apps are still starting much faster than before but the biggest one still take a substantial time. Worse, we have lost all visual and audio clues that something is happening.

inigyou10• 1 month ago

It's interesting how many people don't like the XP theme. I think it was cool, it was productive yet colorful, but I have to wonder if that's just because it arrived when I was at a certain life stage, the same way I had no problem with the COVID lockdown. We used XP in high school computer class the whole time I was there.

GeekyBear2• 1 month ago

I find this take (from the guy who wrote the Windows task manager while at Microsoft) to be evenhanded.

Windows "SUCKS": How I'd Fix it by a retired Microsoft Windows engineer.

https://www.youtube.com/watch?v=oTpA5jt1g60

tentacleuno• 1 month ago

I imagine that the database for the online file association service for Windows XP has been lost to time, but for those who remember it: was it any good?

It seems like quite a good idea now -- if I remember correctly, Windows as of current seems to suggest a generic Bing search, which brings up all the spam "What extension is XXX?" sites.

That could have changed; I haven't really used Windows after 11's debut.

reddalo3• 1 month ago

If I recall correctly, it was pretty bad. It used to open Internet Explorer on this page: http://shell.windows.com/fileassoc/0409/xml/redir.asp?EXT={e... where {ext} was the extension.

Suggestions were vague and they only made sense with well-known filetypes.

There's a screenshot of how it looked here: https://protoweb.org/wp-content/uploads/2025/08/screen.jpg

formerly_proven2• 1 month ago

Today that page would be titled "Microsoft Windows Copilot File Associations"

The more things change, the more they stay the same.

varun_ch• 1 month ago

this might be the only place where a redirection to bing provides a much better UX than what was there previously!

jamesfinlayson2• 1 month ago

I thought in the deep dark paste it used to take you to filext.com but it's been probably 20 years since I intentionally clicked on the link.

izacus• 1 month ago

I don't remember it ever finding anything. Similar to the find driver dialog (until Win10 or so).

vivid242• 1 month ago

I like your Windows postings, please don’t stop!

donatj• 1 month ago

I wish this was more of a full tour than a random sampler of Windows versions. For instance I feel like Windows Me introduced the online search but it's been like... 26 years... since I've used it.

Now there's a big gap. I don't have access to anything between Windows XP and Windows 10. So, Windows 10 (2015) is next

I'm guess these are just what the author already had set up. They're not really difficult to find or set up in a VM...

amadeuspagel• 1 month ago

Sadly, I don't know anymore what kind of web service that was.

I don't know that either, but I remember there were websites specifically for that purpose, where you could look up a file extension and what program to open it with.

Dwedit• 1 month ago

Something went horribly wrong on my computer and it takes about 2 minutes for that dialog to load.

netsharc• 1 month ago

raplayer.exe is stirring up some nostalgia...

brewmarche• 1 month ago

I wonder why in Windows 10 and 11 there is no obvious way to cancel this dialog. You can press Esc, but there are no buttons to do it.

discostrings• 1 month ago

It also closes when you click/tap outside the dialog, unlike most other Windows dialogs. I actually can't think of another Windows dialog with the same level of functionality that behaves this way.

I'm pretty sure it was introduced in Windows 8 along with swipe gestures from the sides of the screen (like the "charms bar") with the tablet use case in mind and with little consideration given to the mouse experience.

petee• 1 month ago

On Win 11, if you disable the Vibe Notepad it refuses to let you associate .txt files to any program, and popups an error. Instead you have to go turn off a specific file association toggle elsewhere (as i recall) only then you can you reassign it

airstrike• 1 month ago

Good post but those images are way too small for me to see anything without having to open a new tab or navigate away, neither of which is fun to do when there are 10+ images

bombela2• 1 month ago

Click on the picture to open the full size version. Click history back to get back to the text.

I noticed I am afraid of clicking without opening new tab today because so many times the UX is broken and loses it's spatial position.

1970-01-01• 1 month ago

They finally made a CLI version of it a decade ago and it works exactly as it should when setting up a new system with a script.

https://learn.microsoft.com/en-us/windows-server/administrat...

Krssst• 1 month ago

Fun fact: on modern Windows, if you uninstall modern notepad using the Settings app to get the old one, you won't be able to associate .txt files with notepad.exe without a registry trick: https://superuser.com/questions/1750222/how-to-open-file-typ...

hulitu7• 1 month ago

Modern Windows has big problems with file associasions: default to web browser, sometimes asks, sometimes it chooses a random program (for images). Old Windows (9x, 2k, XP, 7) was better.

HappySweeney• 1 month ago

A bunch of links open a hardcoded browser (like help links within Visual Studio). Executives have OKRs to meet.

1bpp• 1 month ago

What were the internal politics at Microsoft at the time that resulted in the .NET branding being pushed more aggressively than Copilot today, everywhere from the login screen to file associations?

nailer3• 1 month ago

Not ex-Microsoft, please answer if you are, but fear of Java becoming a universal runtime.

stavros• 1 month ago

Windows has had a few of these "look online" options for decades now, to look up unknown extensions, to find drivers for unrecognised devices, etc. Not a single time in the many, many years of using Windows did any of those ever find anything useful for me.

I'm pretty sure Microsoft just put them in there to mock us.

rkagerer2• 1 month ago

This is such a typical pattern of enshittification from Microsoft. Something Windows 3.1/95/2000/XP made easy - adding a File Type Association - became increasingly contorted over time.

If I recall correctly, in Windows 7 they removed the File Types Manager and you had to either edit the registry directly to adjust existing associations, or resort to a third party app.

By Windows 10 even simply creating a new association for an unrecognized extension seems to require more clicks and scrolling down to a hidden option.

I would love to meet the mastermind morons behind this himan-unfriendly UI and give them a piece of my mind.

nailer3• 1 month ago

I swear they used to have a feature which offered to find a program that would open that type of file from the internet - it NEVER worked, but they did have the feature.

Windows UI evolution: Clicking an unassociated file

Related Stories