I wrote this back in April 2012 for ReadWrite.com.

After watching Microsoft lurch towards completion of Windows 8 and trying out a few of its early versions, I am struck by a tremendous sense of déjà vu. It took me some time to figure out why I was feeling this way, and then it hit me: Win 8 is on track to become the OS/2 of its era, and suffer a similar and ignominious fate.

Don’t get me wrong: I was a big OS/2 fanboy. I even wrote a book about OS/2 in the enterprise, which was never published. But I think it is useful to recall the mistakes of computing yesteryear and see if we can try to avoid them in present-day 2012.

Back in the late 1980s, Microsoft worked with operating systems designers at IBM to produce a successor to the venerable DOS. OS/2 attempted to solve a real problem: having only 640 kB of RAM for running your programs. This meant that DOS made it hard to do more than one thing with your PC at any given time. That’s right: we are talking kilobytes, which is about the amount of RAM in your average coffeepot these days.

Back then we had various tricks to run other things in memory, or to extend that meager memory space, but they weren’t easy. But this was all to get around what was the underlying real issue: being able to run multiple programs concurrently and switch easily among them. We take that for granted today, and indeed with the average multiple-monitor desktop rig that looks like it belongs on the desk of an air traffic controller we run dozens of programs and have all sorts of things open at any one time.

By the time OS/2 was finished, which was a long slog as hundreds of coders worked in dozens of cities around the world, it was basically irrelevant. Windows did a much better job of doing multi-tasking anyway. Intel had come out with better chipsets too, and the world had moved on.

All this meant that IBM and Microsoft were serving different masters when they worked on OS/2. No wonder that they had trouble reaching common ground and ending up splitting up, with Microsoft developing Windows and IBM trying to continue to improve OS/2.

Now look at what is going on with Windows 8. It also began its life trying to solve one problem (having the same OS on desktops, tablets, and phones) but really trying to solve something else: how to beat Apple with a better tablet OS. That doesn’t bode well. We have already had the misfire of Vista behind us, an OS that no one could love or care about. All that Vista accomplished was to put XP more firmly in our minds and keep longer on our desktops. Could an OS really serve two masters equally well? Wait a minute, didn’t I just answer that question?

One of OS/2’s problems is that its protected mode was very bad at running legacy apps. Almost none of the DOS apps ran on the first several OS/2 versions. Sound familiar? Win 8 is also having its problems running legacy Windows XP apps too.

When OS/2 was being built, most people were using 8-bit apps and didn’t really care much (unlike the tech writers) about the move towards 16-bit computing. Because of the upgrade, it was hard to find OS/2 drivers for peripherals such as printers. In my book from 1988, I had written, “UNIX has been able to offer just about everything OS/2 intends to offer for more than a year.” Little did I know how Unix would find its way inside the Mac OS and how Linux would take off in subsequent years. Now we are used to the world of 32-bit and having trouble caring about 64-bit apps, and we have issues still finding drivers for 64-bit Windows. Hmm.

Win 8 also has two different personalities, the old style “Start” that it inherited from XP and the new “Metrosexual” button display that seems to have inherited from Windows Mobile. OS/2 started out with a simple text-only task switcher and quickly got a graphical UI that was crude and something that looked like something from a mainframe terminal designer.

As Nokia and Microsoft work on Win 8, they might end up going their separate ways too, with one doing an OS optimized for phones and the other for PCs and tablets.

OS/2 came with communications and database servers built-in, at leas tin the IBM version. But these were ahead of their time. Now most OS’s have full comms and database capabilities. Ironically, one of the hardest challenges that many business app developers have with the iPad is the lack of a built-in database and the APIs to access the same.

So will Win 8 be more like OS/2 or XP in terms of success? The similarities are somewhat chilling. In the perspective of 2020, I’d say yes.