Fair warning: There are big screenshots in this article. I have kept them full size, and not cropped them at all. Some of you on lower resolutions or mobile devices may need to do a little scrolling to see them all. But I like big screenshots.

On occasion, I like to shake up my computing experience – typically in, what many people feel is, darmatic ways. Only using a terminal. Only (or, at least, primarily) using one type of computer or Operating System.

I do this for a lot of reasons – it gives me insight into the ways we can improve computing, forces me to look at my preconceptions of how I (feel I) need to use my computers, and helps me better understand computing history and the way others interact with computers.

But, mostly, I do it for fun. I get a kick out of it. Always have.

Being cooped up in the house for the last month (and change), I decided to spend a week using – as my primary system – an OS that, while I was intimately familiar with already, I hadn't tried to use as my primary OS in quite some time:

Windows 3.11. Windows for Workgroups.

I know. Many of you are instantly mocking. But, you know what? For the most part… the experience hasn't been all that bad.

Will I be continuing to use Windows 3.11 as my primary system after today?

Oh, heck no.

But, in all honesty, I've used worse Operating Systems. Even modern ones. And, while there were some problems and annoyances with attempting to use this OS in 2020… it was kinda fun!

I used, primarily, two computers over the course of my week in Windows 3.11:

  • My 486 Desktop PC (32MB RAM, 500MB HD, Soundblaster 16). Running Windows 3.11 on top of MS-DOS 6.22.

  • My laptop, running Windows 3.11 within a virtual machine configured with similar settings.

As far as Windows 3.x machines go, this is nice and beefy. I wanted the premium experience here.


Let's start with the biggest problem, right off the bat: Being on-line.

Luckily, Windows 3.11 does provide a full TCP stack supplied by Microsoft.

Within most virtual machines (Virtual Box and QEMU at least) the emulated ethernet adapters work great with the drivers provided with the Win 3.11 installation disks. So getting the Virtual Machine version of Win 3.11 connected to the Internet was easy-peasy.

My 486, likewise, was a similar process as I had access to an old ISA Ethernet card with DOS and Windows drivers. Boom, I'm online. Very little hassle.

1993 technology, 2020 broadband speeds. It's a beautiful thing.

Which brings us to the problem…


A few things are worth noting in that screenshot:

The first is that, yes, we have Netscape Navigator. It runs. Fast. And, when you type in a URL for a website that uses plain old HTTP… it works great. (Assuming no need for fancy Javascript or new-fangled CSS.) There's also older versions of Internet Explorer, Mosaic, and other browsers available.

But anything that requires modern SSL? Simply won't work. At all. In any web browser available for Windows 3.11.

Which means just about every website on the planet (even ones that don't require user accounts) will simply fail to load.

It really stinks.

Luckily, I was expecting this (not my first rodeo), and had other ways to get online ready…


Microsoft shipped Windows for Workgroups with a built-in Telnet client. That still works like a charm in 2020. Connected to my BBS right away.

It wasn't perfect. ANSI emulation wasn't really there. And limited file transfer options. Luckily I also had FTP to move files around.

The ability to use Telnet also allowed me to connect to the shell of my Linux computer. Which, in turn, allowed me to do anything you can do from a Linux/UNIX terminal. Which is quite a lot… including the ability to browse the web using terminal applications.

Right about now, you might be saying, “Telnet into your Linux box?! Why not use SSH?!!?!”

Because, like HTTPS, SSH requires SSL.

And SSL, as a specification, changes like the wind. And, everytime it changes, old versions of SSL become instantly incompatible. Which means old software, even if it uses SSL (or other forms of encryption) are made completely incompatible with newer servers in an incredibly short period of time.

Some say it's worth it, because of security concerns. And, while I see their point (and agree… at least on some level), the lack of backwards compatibility here feels an awful lot like forced, planned obsolescence. Which I don't love.

Oh, and let's get to something that I both love and hate. Installing software off floppies.


This is the installer for Microsoft Office 4.3 – which, I feel obliged to point out, is the best version of Microsoft Office ever made. Fast, light (compared to newer stuff). Does what it does, and does it well. Wish newer office suites were more like this old one.

But, take a look at the progress bar. 62% of the way finished installing. Currently on floppy number… 15.

Yeah, swapping out over 20 floppy disks to install Office gets old. For the first few disks, it's actually a nice experience. The pleasant “click” of the floppy into the drive. The enjoyably tactile experience of ejecting. The sound and subtle vibrations of the disk drive. The slow but steady progression of the bar as it inched ever closer to 100%.

Somewhere around floppy number 8, as I realized I was not yet half way through, my delight transformed into “get this over with already.”

The Floppy Swapping Dance is nothing new and is certainly not Windows 3.x specific. It's just so rare that we need to do it nowadays. Even when I use most “retro” computers, I am typically using machines from the 1980s… where systems and games tended to come on no more than 4 or 5 floppies. I tend to forget that there was a time, especially in the early to mid 1990s, when 20+ floppy sets for a single program were not uncommon.

Around floppy 15 or 16, as my irritation levels began to rise, I realized something. Modern software often takes even longer to install. New games. New versions of Windows. New office suites. Heck, this includes some Linux variants. Often (not always, but often) they take significantly more time to install than this 20+ floppy edition of Microsoft Office. Even taking the time it takes to manually eject and swap floppies into account. Yikes.

Instantly made me feel a whole lot better about the floppy dance.

Eventually, the installation finished. And, from then on, Office 4.3 ran like a champ. Wrote a few articles on it (and then copied them up to my main Linux rig via FTP – which then posted to my server via more secure means).

I'll be straight with you: The writing experience was extremely nice. Nicer than any modern word processor I've used (at least the GUI ones) in many years. Enough features to get my job done – but not too many. Simple interface. Not too distracting. That I had to jump through hoops to get the articles posted was a mild irritant (one that was more thanks to the SSL issues than the office suite). But not bad.


That screenshot? That's Flying Toasters. A screensaver provided by After Dark.

You'll note that I have the music turned on and have the screensaver set to karaoke mode. Yeah. That's a thing. And it's awesome.

Aside from goofy screensavers, I added in a few games. Civilization 2 (the original release had Windows 3.1 support). Indiana Jones Desktop Adventures. SimTower. While many of the big games releases of that era were DOS specific… there are a few Windows 3.1x gems here and there.

Enough to bring a pretty hefty smile to my face.


At the start of this article, I said that I would not be continuing to use Windows 3.11 as my primary system after this week long excursion. And, that's true.

But… well… here's the thing…

As I get ready to turn my attention back to living in Linux (as my regular computing home), I'm actually a bit sad that my Windows 3.11 time is ending. I miss it already.

It's Simple. But with enough features to get the job done.

It's Fast.

It's Semi-sorta-stable (most of the time).

Are there more cutting edge, impressive systems out there? Yeah. Really are. Lots. But, doggone it, Windows 3.11 is so… pleasant. Comfortable. You can really wrap your mind around everything the system has to offer.

Perhaps that says something about me. Or, perhaps, that says something about the pleasant-ness of this nearly three decade old version of Windows. About how it feels. About the joy it can bring… even while being irritating.

I wonder what the experience of using Windows 3.11 would be like… if we got an up-to-date SSL and a web browser (even an old one) updated to use it.



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