Windows UI evolution: Clicking an unassociated file

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2026-06-20

(I don’t plan on doing lots more of these Windows UI blog posts. I just
came across this and found it interesting. Besides, it’s super hot where
I live and I can’t do anything meaningful anyway, so here we go.)

Let’s open the file manager and click on a file that is not a .EXE or
something known to the system like .TXT. What happens?

I don’t have access to each and every version of Windows under the sun,
only to a few of them. Let’s have a look at those.

I also translated some of the German labels into English, but it’s
quite possible that these buttons are called a little differently in the
original English versions.

In Windows 386/2.11 (1989), you just get a “nope” (translation of the
image: “ABC.OMG is not executable”):

This version of Windows already had the concept of “open file type
$foo with program $bar“, but apparently there was no UI to configure
this. Or I couldn’t find it. You could set up the associations in
WIN.INI:

Windows 3.1 (1992) improved the situation a little bit:

It still just tells you “no”, but it now also tells you that there is a
concept of file type associations and where to configure them. This gets
you to a basic but functional dialog window:

The text box at the top lets you enter the filename extension, the list
box at the bottom allows you to select one of the installed programs. If
it isn’t in the list, you can hit the “Durchsuchen…” (“Search…”) button
to select an arbitrary program.

Windows NT 3.1 (1993) is basically the same (as is Windows for
Workgroups 3.11, by the way):

Windows 95 (1995) was a big step up, because you now get a dialog window
where you can select the desired program right there — no need anymore
to navigate someplace else:

If the program isn’t listed, you can hit the “Andere…” (“Others…”)
button to select a program directly.

This behavior remained the same in Windows 98, Windows ME, and Windows
2000 — here’s the latter:

And then Windows XP (2001) came along and it now tried to nudge you to
use some kind of web service, because The Internet was “finally”
everywhere™:

Sadly, I don’t know anymore what kind of web service that was. If you
do, please tell me. It was most likely run by Microsoft, but what was
its database? Which programs did it list? How did it query this database
— did it upload the entire file or parts of it or just the filename
extension? Did it offer to install a program on your PC? (I vaguely
remember that this service was used as an attack vector of some kind and
that magazines wrote “don’t use this!!1!”, but I’m not sure anymore.)

–edit: Okay, as a reader told me, this did nothing but open a website
in Internet Explorer, sending the filename extension as a query string.
The service has been shut down since 2006, they say. And it was pretty
useless, apparently. The reader speculates that only Microsoft-certified
partners might have ended up here and notes that even popular filetypes
like .3GP weren’t recognized. You can give it a shot yourself by
asking the Internet Archive:

https://web.archive.org/web/20130530100029/http://shell.windows.com:80/fileassoc/0404/xml/redir.asp?EXT=3gp

Local copy of a
screenshot from the Protoweb archive
(reduced in size):

If you didn’t want to use that service, you could select the second
radio button to get to the old dialog:

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:

Ouch, we have clearly entered the “everything is flat” era now and you
can’t really tell anymore which items on the screen are interactive.
Even the window decorations are gone. The text at the top (“Im Store
nach einer App suchen” — “Search Store for App”) is actually a button
that you can click (the icon is probably supposed to indicate that?).
“Weitere Apps” (“Other Apps”) is also something that you can click
(indicated by the color, like a web link) and it opens a list:

Again, this shows the installed programs. Sorry, they’re called “Apps”
now. What you might not be able to tell immediately is that you can
scroll this window to reveal the third option:

If the list doesn’t contain the program that you want, you can click the
button/text/whatever “Andere App auf diesem PC suchen” (“Look for
different App on this PC”).

And that’s it. I don’t have access to any other versions of Windows.

Enjoy summer. 🥵