Backward compatibility in operating systems

Earlier this week, Tom Scott posted a video to YouTube about the forbidden filenames in Windows. It’s an interesting subject that comes up often in discussions of computing esoterica, and Scott does an excellent job of explaining it without being too heavy on tech knowledge. Then the video pivots; what was ostensibly a discussion on one little Windows quirk turns into a broader discussion on backward compatibility, and this inevitably turns into a matter of Apple vs. Microsoft. At this point, I think Scott does Apple a bit of a disservice.

If you’ve read much of my material here, you’ll know I don’t have much of a horse in this race; I’m not in love with either company or their products. I’m writing this post from WSL/Ubuntu under Windows 10, a truly unholy matrimony of software. And while I could easily list off my disappointments with MacOS, I genuinely find Windows an absolute shame to use as a day-to-day, personal operating system. One of my largest issues is how much of it is steeped in weird legacy garbage. A prime example is the fact that Windows 10 has both ‘Settings’ and ‘Control Panel’ applications, with two entirely different user experiences and a seemingly random venn diagram of what is accessible from where.

This all comes down to Microsoft’s obsession with backward compatibility, which has its ups and downs. Apple prioritizes a streamlined, smooth experience over backward compatibility, yet they’ve still gone out of their way to support a reasonable amount of backward compatibility throughout their history. They’ve transitioned processor architecture twice, each time adding a translation layer to the operating system to extend the service life of software. I think they do precisely the right amount of backward compatibility to reduce bloat and confusion1. It makes for a better everyday, personal operating system.

That doesn’t make it, however, a better operating system overall; it would be absurd to assume that one approach can be generally declared better. Microsoft’s level of obsession in this regard is crucial for, say, enterprise activities, small businesses that can’t afford to upgrade decades-old accounting software, and gaming. There is absolutely comfort in knowing that you can run (with varying levels of success) Microsoft Works from 2007 on your brand new machine. It’s incredibly valuable, and it requires a ton of due diligence from the Windows team.

So, this isn’t to knock Microsoft at all, but it is why I think dismissing Apple for a lack of backward compatibility is an imperfect assessment. I’ve been thinking about this sort of thing a lot lately as I decide what to do moving forward with this machine – do I dual-boot or try to live full-time in Windows 10 with WSL. And I’ve been thinking about it a lot precisely because of how unpleasant I find Windows2 to be. Thinking about that has made me examine why, and what my ideal computing experience is. Which is another post for another day, as I continue to try to make my Windows experience as usable as possible. Also, I’m not in any way trying to put down Scott’s video, which I highly recommend everyone watch; it was enjoyable even with prior knowledge of the forbidden filenames. It just happened to time perfectly with my own thoughts on levels of backward compatibility.


  1. Apple has absolutely let the ball drop in the areas of bloat and confusion in other ways, but I maintain that it would be far worse if they attempted the level of backward compatibility that Microsoft does. ↩︎
  2. Like many, I believe Windows 7 was the peak of the OS. Windows 10 is… eh. At least we have WSL. And, FWIW, I believe somewhere around OSX 10.6 was where Apple peaked. ↩︎