Windows and its discontents

I generally try not to write about things I dislike, but this time I will make an exception. This post acts as an outlet to vent my immense frustration with the infamous Microsoft OS on a less transient medium than Twitter.


Important qualifications to my rant:

  • No operating system is perfect. Mac, Linux, iOS, and Android all have design flaws, bugs, seemingly illogical choices, and use cases where they don’t work well. However, over the years, these other systems seemed to have bothered me way less than Windows.
  • I’m an academic and I normally use a Mac as my main workstation and Linux on servers. Windows and Office are the only Microsoft products I see daily because I am forced to use them at work.
  • I am a computer scientist by training, I studied some HCI, and probably that’s why I can’t tolerate easily fixable flaws in IT systems.
  • I don’t dislike Bill Gates personally, and I think he’s smarter and more civically minded than big tech entrepreneurs who prefer teenage fantasies about colonising Mars to boring, frustrating endeavours like fighting malaria in low-income countries. I also don’t think he is a Jewish lizard from outer space who wants to depopulate the world through 5G-powered fake vaccines covering up the whole plan with Covid-19. I just wish he got fantastically rich by selling a slightly less crappy OS.
  • Microsoft is a large organisation that I’m sure employs many brilliant engineers, designers, and experts of all sorts. I’m sure that the company produces many new amazing information technologies and actual innovations that are managed in a completely different way to its OS. Unfortunately, these are not the sides of Microsoft I experience on a daily basis.
  • In fairness, Windows 10 shows marked improvements compared to previous versions, and so does Office 365, OneDrive, and the new products that were shamelessly ripped off from show some interesting similarities to Google Docs and Dropbox.
  • Some issues might be related to my particular hardware/software set-up and not apply to anybody else. I have no way to ascertain that but it doesn’t make my daily issues less irritating.
  • I find most OSs better than Windows, Gmail is infinitely better than Outlook, but the same doesn’t apply to MS Word and Powerpoint. LibreOffice is frankly embarrassing (some open source fanatics might disagree but let’s face it) and Google Docs doesn’t have enough features to compete yet. That said, MS Office is full of bizarre defects that might be easily fixed, considering that it’s been actively developed for 38 years, which in software terms is like a geological era.
This post is dedicated to the memory of Clippy

Let’s get down to business. Here’s my list:

  1. Outlook invitation emails disappear when you accept/decline: Why? Surely these emails could stay in the inbox with no harm, allowing me to keep track of meetings I have declined.
  2. In Outlook, some declined events disappear and I don’t understand why. Declined events should stay in the calendar to remind me that some meetings are happening (even if I’m not going).
  3. Why is the panel to switch between Mail and Calendar at the bottom of the interface, even on the desktop version (while I admit it might make sense on a mobile version)?
  4. Why does Outlook show email threads in 3 modes: collapsed, expanded, and semi-expanded? The semi-expanded mode is totally confusing and useless.
  5. Outlook Calendar changes the colour of the calendar randomly every time you hide/show them. Why? Is it done deliberately to annoy the user?
  6. Outlook still does the “reply to myself” thing that is very 1990s. What is the use case where the user wants to reply to themselves? It could be fixed with an “if” block somewhere, I’m sure.
  7. In Outlook for Mac, all events in the calendar are described with the text “Name Surname: You are the organiser”. A better option would be “Name Surname is the organiser”. In most cases, I am not the organiser and “you are the organiser” is a stress-inducing message.
  8. In Outlook Calendar, today and past days are not visually different from any other day in the calendar. I would humbly suggest that, despite seeing the attractions of eternalism as a philosophy of time, in most practical scenarios that involve the use of a work calendar, today is more important than any other day, and the future is more important than the past. To make the calendar more usable it is possible to change today’s events to different visual style, but this forces the user to struggle with one of the buggiest, least usable things ever created: the conditional formatting panel, a space-time warp where boolean logic doesn’t work.
  9. Sharepoint and OneDrive are two different products/platforms that actually look identical to me. How are they different? The links to share files/folders are very long and ugly. Why?
  10. This might be my employer’s IT, but Outlook fails to connect to the server on a regular basis. It reminds of downloading emails on POP3 on a 56K line in the early 2000s.
  11. When clicking on a zip, Windows opens it without unzipping it in an interface that is nearly identical to a normal folder. My “digital native” students constantly struggle with this, thinking they unzipped the file while they are working on temporary files. What’s the advantage of not unzipping archives immediately when clicking on them, unless they are extremely large?
  12. I once used a Windows server. It slowed down constantly for no reason, despite being on very fast hardware. I gave up.
  13. I am really puzzled about the fact that Windows shows file without their extensions by default (“report” instead of “report.pdf” or “report.docx”). How is hiding extensions supposed to help the user? Isn’t just clearer to show the file name with its extension? What’s wrong with “report.pdf” and “article.docx” and “holiday2019.jpg”? I have always found this horribly confusing and even potentially dangerous for security (I remember many “myhotpicture.jpg.exe” attachments in the 2000s). It seems that this terrible idea has also been adopted by Apple[Update: I am told that this approach aims at avoiding users accidentally changing the file extension. It might make sense, even if it never happened to me.]
  14. The sound card on my Windows laptop malfunctions regularly every few hours and makes crackling sounds. The only fix is to reboot Windows. One of the effects of this issue is making the Bluetooth mouse lag. No fix currently exists (apart from throwing the laptop against a brick wall at high speed while screaming).
  15. Why OneDrive doesn’t remember and suggest the shared files I opened recently? Just to force me to search for links in old emails and experience the subtle pleasures of the search panel in Outlook?
  16. MS Word has been developed for 35+ years and yet its writing support tools are almost non-existent. It barely finds typos and suggests synonyms that are usually irrelevant. Anything involving modern NLP/AI like Grammarly is not even contemplated.
  17. MS Teams is ok, but why doesn’t it have a grid view like Zoom? Why the limit of 4 video feeds that get constantly re-shuffled? Why do Teams meetings have long, horrible URLs as opposed to a neat shortcode/ID like in Zoom?
  18. MS Teams shows a button to join the meeting that I am already in. An “if” block somewhere could fix it.

    checking for a solution
    The solution to the problem, alas, will never be found.
  19. The Teams’ control panel often appears on the person’s face and cannot be moved/hidden. I spend hours talking to people with a camera icon on their mouths.
  20. Windows 10 is full of legacy interfaces and panels. Wouldn’t it be easier to just make that stuff from scratch with a coherent visual style, rather than occasionally re-using icons from Windows 2000 for unknown reasons? Microsoft should have enough capital to invest in this endeavour.
  21. Windows Explorer crashes and restarts, losing track of the open folders. That is incredibly irritating and happens at least once a week.
  22. Windows 10 crashes. Properly. I get a blue screen every couple of weeks. Thanks to Dropbox and other cloud services I don’t lose any work, but it is incredibly annoying. The blue screen now has a QR code and a cute “:-(“, but this hardly makes it tolerable in 2020. On a Mac, I can recall 2-3 full crashes in 10 years.
  23. When an app freezes or crashes, Windows says that it is “looking for a solution”. It never ever finds one. Learning from repeated failures, it might make sense to stop looking for these hypothetical solutions and just let the app crash, without pretending that anything can be done about it.
  24. The hierarchy of the Windows file system is unclear, to the point of looking deliberately designed to bamboozle users. The “home” folder, which is extremely prominent on Mac and Unix platforms, is basically invisible. “Documents” is a meta-folder that aggregates other folders through an opaque logic. “This PC” shows only meta-folders and not the home folder.
  25. Windows 10 has broken away from the time-honoured tradition of Windows restarting itself to upgrade in the middle of important meetings. This is remarkable and I sincerely thank Microsoft for this innovation. They could have figured this out 20 years ago, but better late than never.
  26. Why using “\” in paths when that is also the escape symbol in most languages and encoding systems and not “/”? Why allowing spaces in important folder names like “Program Files”? Just to drive programmers crazy?
  27. Why does my Windows laptop start overheating when being idle? It happens to me regularly. I close the laptop and hear the fan screaming for hours.
  28. Why the recycle bin is still the most prominent icon on the Desktop? Why not have the home folder or something usually more important? It would be like putting the bin in the middle of your living room rather than in a hidden corner.
  29. Bash on Linux/Unix is a shell featuring some very old-fashioned syntax, but it’s powerful, consistent, reliable, and fast. I can process hundreds of GB of data with shell command pipelines without any glitch. Windows shells (Cmd, Command, or Powershell), by contrast, are irredeemably awful, looking like cheap copies of Unix shells hacked together quickly (which is probably exactly what happened in the 1980s). Even basic OS commands like “COPY” (that copies files) don’t work as expected: COPY fails on large folders for no apparent reason, and people suggest using XCOPY (a fancy version of COPY that actually works). How can a core command in the system be so buggy?
  30. Why does Windows show an icon when using a VPN? It would be pretty damn useful to remind the user which VPN they are connected to, without having to dig into the control panel every time.
  31. On Word and Powerpoint it is impossible to control the compression level of images. When exporting a document to PDF, Office for Mac fails to compress the images and I get 100MB PDFs, while on Windows it compresses them too much and I get 1MB PDFs with grainy images. Why not letting the user decide what to compress and how much depending on the context?
  32. When I type names in Outlook, it never finds the right people, particularly when external to the organisation. If I want to contact John Doe, I occasionally see it by typing “d” and never “j”, but this behaviour is unpredictable. I often end up having to search for the person and copy-paste the email address.