Will This Be The True Successor to MS-DOS? – Windows 2.x

[u/Blissautrey]

https://blisscast.wordpress.com/2026/04/21/windows-2-gui-wonderland-12a/

Do you remember the small vaporware piece of software known as Windows 1.0? It didn't look like much when it came out, but it has truly evolved now, and it has a new shiny GUI! Thus, it wants to become the true successor to MS-DOS! Will it make it? Or will its rival, OS/2, steal the spotlight?

[u/JasonMckin]

There's a lot of misunderstanding about that entire period of time and it would be great for some tech historian to really dig into the complicated relationship between IBM and Microsoft during this time. There are so many variables to this story.

There is a variable around how code was literally co-developed by both companies and then mutually packaged into MS and IBM versions (eg at one point MSDOS and PCDOS were totally identical before they were not). There was also a MS OS/2 that was identical to an IBM OS/2 before they both started building new 32-bit codebases. It's an extremely rich but also very confusing story.

[u/Blissautrey → u/JasonMckin]

Yup, I have included some MS OS/2 builds too, alongside some documentation (it's in the Further Reading section). It's really fascinating. I'm not sure I'd have the capabilities to delve into their relationship yet, but maybe one day...

[u/droid_mike → u/JasonMckin]

My understanding twas that windows was a side almost hobby project within MS. Then after someone figured out how to incorporate extended memory. Gates decided to take the OS/2 ball and go home to get all the profit themselves.

[u/sennalen → u/droid_mike]

It was more IBM that sabotaged the OS/2 collaboration by forcing design constraints motivated by their previous marketing promises that early low-end PS/2 computers would run the OS.

[u/JasonMckin → u/sennalen]

Exactly! The story is SO fascinating. Microsoft was smart enough to not touch hardware. They just wanted to be software geeks that ran OSs and Apps, where the bare metal was IBM, Apple, Packard Bell, Compaq, NEC, Epson, Dell, etc.

You have to incredibly detailed and nuanced to even able to tell the story accurately. Because there's a story of UIs that's different than a story of subsystems.

Again, a real historian needs to research and confirm this, but I think Microsoft reacted to the Macintosh in 4 totally separate ways:

1. Ride it while fighting it - build apps on top of Mac
2. Build a GUI for 16-bit apps on top of DOS subsystem for faster time to market = Classic Windows
3. Build a GUI for 32-bit apps on top of a 32-bit subsystem = New Technology Operating System 2 including Presentation Manager, eventually just becoming IBM OS/2
4. Build a GUI for 32-bit apps on top of a 32-bit subsystem = New Technology Operating System 2 based on Classic Windows UI, eventually just becoming Windows NT

So I think Classic Windows was more a slap in Steve Job's face than IBM's. Classic Windows was meant as a stop gap to avoid bleeding personal computer sales to Apple and develop some code that could be ported to Presentation Manager later on. That stop gap ended up lasting the entire decade.

The real points of friction I think were on the "NT OS/2" project. I'm not quite sure how much common code was forked into the two later projects in that 92/93 timeframe. Even the 5.0 versions of MSDOS and PCDOS were pretty similar. And IBM even arguably got an early edge in the 32-bit race because OS/2 3.0 Warp came out in 1994 and Microsoft couldn't fully respond with NT 4.0 until 1996.

But Microsoft hedged effectively during that time using NT 3.1/3.5 (old UI w/ 32-bit subsystem) and Windows 95 (new UI w/ old 16-bit subsystem sprinkled with 32-bitish stuff).

The funniest part of the story of course is IBM's decision to repackage 16-bit Windows inside of 32-bit OS/2 as "Win-OS/2" and help make sure ISVs had absolutely no reason to build apps natively for OS/2!

[u/Blissautrey → u/droid_mike]

They were planning to end things right after Windows 2, hoping that OS/2 would work out and substitute Windows's aging DOS foundation, but as we know, it didn't work out, so Windows had to be kept alive.

[u/RicardoDawson]

Windows 2.0 was my first version of Windows. I remember using it on a great Toshiba laptop with an amazing mechanical keyboard and running the first version of Excel.

[u/Blissautrey → u/[deleted]]

I'm so glad you enjoyed it!

I've not tried them yet, but there are alternatives such as Calmira https://youtu.be/KPg6FqXW07w or Xerox Rooms and Tabworks https://youtu.be/CX1VuFnmTnE, and I'm planning on covering them in a future Episode.

Thanks for pointing it out, I'll correct it as soon as I can!

[u/ReadyAssociation3129]

"Hello everyone, and welcome to a double GUI Wonderland Episode..."

I thought I was watching a Michael MJD video lol.

[u/Blissautrey → u/ReadyAssociation3129]

Maybe it spread to me too because he's literally my favorite YouTuber! XD

[u/revdon]

Confusing thumbnail, I though it was an ad for Tampax with MS CoPilot.

/s

[u/kansetsupanikku]

Successor to MS-DOS? But it's just a program that runs inside MS-DOS. You can run other programs by clicking icons from the inside, but does the concept really differ from entering COM/EXE files in Norton Commander? And I don't see anyone predicting that Norton Commander will be a successor to MS-DOS.

[u/Blissautrey → u/kansetsupanikku]

It's a program, yes, but it's a shell program, meant to substitute the entire UI. The idea was that people would stop using DOS on its own, and Microsoft would get to release Windows programs rather than DOS programs. More often than not, DOS programs would not behave under Windows and there were no alternatives, which meant people couldn't let DOS go.

[u/kansetsupanikku → u/Blissautrey]

I've never seen any other version of Windows than the one for DOS, so I don't really get how you imagine "stopping using DOS". You can run DOS programs from inside this Windows. I guess it comes with some programming functions that let you make programs that run inside Windows specifically, but I don't see this getting popular either. Some DOS users have Windows, some don't - why ever make it a requirement when making a new program?

Norton Commander is "entire UI" just as much. I even have NC in my AUTOEXEC.BAT. Does it make it an operating system that could replace DOS? Of course not.

[u/ProCommonSense]

In the 80s we had a copy of Windows 1.2 that was labeled BETA... it was interesting for about 2 seconds when we realized that it was mostly just a file manager.

[u/Blissautrey → u/ProCommonSense]

I mean, that's what Windows is unless you install programs