Windows UI evolution: Clicking an unassociated file
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Windows UI evolution: Clicking an unassociated file
2026-06-20
(I don't plan on doing lots more of these Windows UI blog posts. I just<br>came across this and found it interesting. Besides, it's super hot where<br>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<br>something known to the system like .TXT. What happens?
I don't have access to each and every version of Windows under the sun,<br>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<br>quite possible that these buttons are called a little differently in the<br>original English versions.
In Windows 386/2.11 (1989), you just get a "nope" (translation of the<br>image: "ABC.OMG is not executable"):
This version of Windows already had the concept of "open file type<br>$foo with program $bar", but apparently there was no UI to configure<br>this. Or I couldn't find it. You could set up the associations in<br>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<br>concept of file type associations and where to configure them. This gets<br>you to a basic but functional dialog window:
The text box at the top lets you enter the filename extension, the list<br>box at the bottom allows you to select one of the installed programs. If<br>it isn't in the list, you can hit the "Durchsuchen..." ("Search...") button<br>to select an arbitrary program.
Windows NT 3.1 (1993) is basically the same (as is Windows for<br>Workgroups 3.11, by the way):
Windows 95 (1995) was a big step up, because you now get a dialog window<br>where you can select the desired program right there -- no need anymore<br>to navigate someplace else:
If the program isn't listed, you can hit the "Andere..." ("Others...")<br>button to select a program directly.
This behavior remained the same in Windows 98, Windows ME, and Windows<br>2000 -- here's the latter:
And then Windows XP (2001) came along and it now tried to nudge you to<br>use some kind of web service, because The Internet was "finally"<br>everywhere™:
Sadly, I don't know anymore what kind of web service that was. If you<br>do, please tell me. It was most likely run by Microsoft, but what was<br>its database? Which programs did it list? How did it query this database<br>-- did it upload the entire file or parts of it or just the filename<br>extension? Did it offer to install a program on your PC? (I vaguely<br>remember that this service was used as an attack vector of some kind and<br>that magazines wrote "don't use this!!1!", but I'm not sure anymore.)
If you didn't want to use that service, you could select the second<br>radio button to get to the old dialog:
Now there's a big gap. I don't have access to anything between Windows<br>XP and Windows 10. So, Windows 10 (2015) is next:
Ouch, we have clearly entered the "everything is flat" era now and you<br>can't really tell anymore which items on the screen are interactive.<br>Even the window decorations are gone. The text at the top ("Im Store<br>nach einer App suchen" -- "Search Store for App") is actually a button<br>that you can click (the icon is probably supposed to indicate that?).<br>"Weitere Apps" ("Other Apps") is also something that you can click<br>(indicated by the color, like a web link) and it opens a list:
Again, this shows the installed programs. Sorry, they're called "Apps"<br>now. What you might not be able to tell immediately is that you can<br>scroll this window to reveal the third option:
If the list doesn't contain the program that you want, you can click the<br>button/text/whatever "Andere App auf diesem PC suchen" ("Look for<br>different App on this PC").
And that's it. I don't have access to any other versions of Windows.
Enjoy summer. 🥵