Fun Fact: Every single Exe today still checks prior to running whether it is Barbie Riding Club (1998) or can it run normally?

Because when you update your OS and your game breaks - you don't blame Hasbro, you blame Windows every time. You can't just call up Sierra Games and ask them to update - they don't exist anymore and so you must carry everything forward - bugs included.

it's why you can't name files certain names such as CON

To expand on this: The reason you can't name files CON, etc., is because of a program from the 1960s called Peripheral Interchange Program (PIP), a program used in Digital Equipment Corporation's computers. The overall OS that PIP was part of was called CP/M.

DOS, which came out in the 80s and was made for IBM computers, was modeled after CP/M, and it kept and expanded the capabilities of PIP.

Then Microsoft came along and created a modified version of DOS called MS-DOS which IBM started using.

Eventually, Microsoft created Windows 95, merging two initially separate products: MS-DOS and Microsoft Windows. Microsoft left in the code for handling CON, etc., but they hadn't put in any limitations for filenames, which caused some bugs. So, from the next version of Windows onward, they disallowed the ability for anything to name a folder or file "CON", among other related things.

So the reason you can't name a file or folder "CON" is because of a 60-year-old file-copying program nobody uses anymore.

That's what happens when your entire business model is promising to support [your business name here]'s favorite feature forever. It makes a lot of money, but boy does it make for a terrible product

At some point last year I had a Japanese program launch a popup window that was clearly from pre-NT Windows. So bizarre.

That looks to be an Access prompt, from the MS office suite. If you've ever written a macro you know how ancient the UI looks behind the scenes with those apps, and this isn't even a main line office app since it deals with databases and they push excel to work with sets of data like that.

So yes it's a Microsoft product, but it's not really native Windows and it's not an app that makes a lot of sense to spend a lot of time developing.

Just for accuracy's sake. I'm certain there are better examples.

Anyways, I'm perfectly fine with dated UI as long as it's efficient and does what it's supposed to do. If they perfected this stuff way back when you had one chance to ship out a working product, is it really necessary to reinvent the wheel just for aesthetics? Cause that's how you get a neutered settings app instead of a fully functional control panel.

Always will be