• First there is the plague of rich text formatting when pasting from the clipboard. It persists by default across all the major applications, which is wrong; the clipboard should copy text as plain text, not rich text. There are many, many times in chat messaging and email where it is obvious that data was copied and pasted and took on an unwanted form. There are very few instances in which this is actually desired. This problem afflicts Skype for Business, Outlook, and OneNote, among others.1 2
  • Related, selecting text for the clipboard is a hassle. You know how it’s hard to select text in iTerm in macOS? Imagine if every major app was that hard to select, and that gives you an idea of how hard it is in Windows 10. By the time you’ve managed to actually select and copy some text, you don’t even care that it’s going to come out as rich text formatting. You’re just thankful you didn’t have to type it out all by hand like a slave. The software makes you work for it.
  • The operating system contains zero rounded corners. This is wrong. It creates mental fatigue. macOS correctly understood early on that rounded corners are important. Andy Hertzfeld:

    Steve [Jobs] suddenly got more intense. “Rectangles with rounded corners are everywhere! Just look around this room!”. And sure enough, there were lots of them, like the whiteboard and some of the desks and tables. Then he pointed out the window. “And look outside, there’s even more, practically everywhere you look!”. He even persuaded Bill to take a quick walk around the block with him, pointing out every rectangle with rounded corners that he could find.

  • Split screens are a nightmare to work with. On macOS, when you have two windows that share a screen, and you go to resize them, they always stay connected, and the blur that occurs on one of the windows is beautiful. On Windows, when you go to resize, an ugly vertical bar is the only thing that appears whilst you move your cursor, and then the windows redraw only when you release your cursor. They divorce very easily too, and while getting them glued back together is achievable, it’s a feat of patience. The software makes you work for it.

  • The methodology for getting to the unlock screen is archaic and idiotic. On macOS you merely tap any key on the keyboard, or move the mouse or trackpad, and you’re presented with the login screen. On Windows, you have to hit a key combination, CTRL + ALt + DELETE, before you can get to the login screen. This key combination is difficult to achieve with a single hand, and there is no need for it. You save no battery by making it harder to get to the login screen - tapping a key wakes up the computer just as much as it does on macOS. Rather, it merely creates an unnecessary step. It’s wasteful. It’s inefficient. Much of the OS is like this. I’m sure there’s a lengthy business explanation about why it’s needed, about how it came into being, about why it makes sense, about why Microsoft can’t get rid of it for reasons X and Y. But you know what? macOS figured out how to not need it, and macOS is used in business a lot, so it’s a solvable problem.

  • There is lunacy in having to open a second window by re-opening the same application. If I’m in Terminal on macOS and I want a new window, I just hit CMD + N. But in Windows, if I’m in Command Line and I want a new window, I have to go to the Start menu, search for it in the cluttered menu system, and reopen the application as though I have zero windows open. This is wasteful and counterintuitive.

  • The OS gets easily confused by having a non-high-density external monitor connected to a high-density laptop display. For example, let’s say you have a Chrome window open on the external monitor, and you accidentally hit CTRL + S, since the keys are mapped incorrectly on Windows. The dialog for saving the window appears at twice the size (i.e. it displays at @2x resolution of what it should be, thereby making it twice as big) because the OS thinks you’re handling this on the laptop high-density screen. Maybe this is just a Chrome bug, I don’t know. All I know is that this sort of thing happens a lot on Windows and it never happens on macOS on an identical setup.

  • And then there is the inferiority of the scrollbars that plague every application in Windows. On macOS and iOS, the presence or absence of a scrollbar within a UI does not affect the overall available width of that UI’s inner content, but it does in Windows 10. This means that text on a web page jumps around when the width changes. This occurs quite often. If you toggle something that adjusts the height of the page content, such that it goes from all fitting above the fold to not all fitting above the fold, you’ll introduce a scrollbar, and thereby inadvertently change the page width, which shifts the entire page content to the left. This also occurs when you open a hamburger menu or modal that overlays the screen and locks it with body: { overflow: hidden }.

There are other problems of course, but these are the ones that I’m reminded of every time I use Windows.

My experience is that most Windows aficionados either have never realized these innate problems with the operating system, or else they’re aware of them but simply don’t think they’re that big of a deal. But if you’ve used macOS for thousands of hours and can appreciate the difference between good software that works for you versus poor software that you must work for, you’ll see a night and day difference between the two operating systems. Windows has had many years to catch up with macOS and it hasn’t. At this point I’m not sure it ever will.

Steve Jobs in 1995:

The problem with Microsoft is they just have no taste. They have absolutely no taste, and what that means is, and I don’t mean that in a small way, I mean that in a big way.

23 years later, this still holds true.


  1. OneNote is truly a train wreck of an app, as is Skype for Business, but I won’t go into app-specific problems in this piece. ↩︎
  2. In fairness, this problem is a scourge for Notes in macOS. It’s largely for this reason I find Notes to be unusable (well, that and its unbearable color scheme and use of text shadow). Notes is one of the weakest applications in macOS. Thankfully it’s the of the very few default apps in macOS that doesn’t adhere to plain text formatting when pasting from the clipboard. ↩︎