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Raymond Chens blog and book (The Old New Thing) is an absolute delight! I always had a big respect for how intuitive the Windows 95 GUI is, and reading his description of the thoughts and methods behind its inception, it's no surprise that it became so good. It seems like Microsoft was extremely pragmatic and reasonable in many of their endeavors back then. It's a wonder how it degenerated into the absolute unit of sh*t that is modern Windows (even if the filesystem and kernel is arguably a lot better, everything on top seems to be developed by an army of interns)

Because, when they did it right, in Windows NT 3.51, the users with legacy 16 bit applications screamed. There was a 16-bit DOS compatibility box, but it wasn't bug-compatible with DOS.

Microsoft underestimated the inertia of the applications market. NT 3.51 was fine if you used it as a pure 32-bit operating system. You could even configure it without DOS compatibility. Few did.

Doesn't Windows setup still use some weird minimal version of Windows? I remember having to hack my employers provisioning once to install virtio drivers and I ended up in this "purgatory OS" where I could use DOS commands to add drivers.

The fact that Windows can upgrade an installation in place with relatively high success is impressive. Is it possible to have an install that's been repeatedly upgraded all the way from MS-DOS without needing a reformat somewhere along the way?

Clearly they should have used QNX for the installer so it would have fit on a single floppy.

I always thought Windows (until 7) looked so lacking in polish around the edges compared to even the earliest versions of Macintosh system software -- especially during install, boot, crash, and shutdown. During boot, for example, even modern Windows boxes [correction: pre-EFI only] show a BIOS screen followed by a brief blinking cursor before the Windows graphics mode takes over. It was much worse in earlier versions.

The Macintosh screen never dropped you into a text-mode console, no matter what. Everything on the screen was graphics-mode, always -- and there weren't glaring design changes between system versions like in Windows (except at the Mac OS X introduction, which was entirely new).

Installing Macintosh system software onto a HDD was literally as easy as copying the System Folder. System installer programs did exist, but in principle all that was happening was optionally formatting the target drive and then copying System Folder contents. So simple. Of course there were problems and shortcomings, but the uncompromising design esthetic is noteworthy and admirable.

I never thought of Windows 3.1 as an OS. The other 2 was MS-DOS and Windows 95.

The "mini" Windows 3.1 it came with was pretty much fully functional though, you could literally boot directly into PROGMAN.EXE as the main Windows 95 shell.

Reading these comments is like seeing revisionist history. Windows 95 was the biggest piece of crap. The thing crashed constantly. Windows 11 today looks better and runs better. There is simply no comparison. Anyone who says different has no idea what they are talking about.

I remember the talk back then was: "The better way is to install Windows 95 on top of DOS."

If they were going to install a bare Windows 3, they could at least make an effort to ship a bare 95.

Don't modern versions of Windows do the same? For example, I clearly remember that the Windows 10 installer first launches a Windows 7-like environment.

It seems also answer https://retrocomputing.stackexchange.com/questions/14903/why... this.

> Raymond has been involved in the evolution of Windows for more than 30 years. He occasionally appears on the Windows Dev Docs Twitter account to tell stories which convey no useful information.

Way to go Mr. Raymond!

I love that little nugget of info at the end. You could originally run excel standalone without an OS and it came with windows 2.1 bundled

There's really something missing today as opposed to the 80s and 90s : back in the days, you had new computer brands coming out every year, with they own OSs and hardware... It really was a perpetual amazement and joy. Of course at that time i didn't have to work with all those things, which made any compatibility issues not that important to me.

Yet i wonder : how can we relive through those enjoyments ? It was a bit similar when mobile phones started, but it settled much quickly, without leaving any but 2 survivors for the last decade. What makes it so hard today to release new hardware+software for the mainstream market ?

I still have my Windows 95 installation floppies. It was a phenomenal operating system at the time, but I don't miss it one bit.

I was looking for a blogpost from many years back about features Windows cannot provide, because it would result in logical inconsistencies if multiple applications used the feature. The blogpost gave examples like setting the desktop background or file-application associations "definitively" from applications, and mentioned at least one example of two applications fighting resulting in some chattering in the Windows UI.

I thought it was Raymond Chen's blog but I haven't been able to find it. I thought someone here might recall and have a pointer.