Windows UI evolution: Clicking an unassociated file

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

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...

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.

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.

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

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

> 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.

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

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

raplayer.exe is stirring up some nostalgia...

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).

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