Broken Windows 10

Is Microsoft facing another cliff in market share?

If you own Microsoft shares, you should seriously consider selling it.

Anger against Microsoft has been building up for quite some time already. Each time they update Windows 10, something breaks, resulting in disruption to millions of their users. This has been going on for a couple of years already, which seems to indicate that they have a systemic issue with their engineering and testing process.

It all started in 2018. Microsoft had to suddenly withdraw their October 2018 Feature Update. There were reports that there was a bug in the update process, resulting in users’ documents disappearing after the update. That was an outrageous error on Microsoft’s part. But at that time, you could have brushed it off as a one-off screw up in Microsoft’s part.

But since then, software outages keep on happening after each update.


Eventually, every Windows 10 update is met with trepidation instead of excitement. Each time users update Windows 10, they pray and hope that nothing will break. Over time, as more and more people experience problems (ranging from minor annoyances to total catastrophe), outrage against Microsoft gradually builds up.

What is going on in Microsoft?

Eventually, the story emerged that starting from 2014, Microsoft made their in-house professional Quality Assurance (QA) engineers redundant and crowdsourced QA to amateurs. This turned out to be a BIG mistake. Windows 10 is a monstrosity. It has gotten so colossal and complex that there is not a single person in this entire universe who can fully understand it under the hood. Testing Windows 10 is a job that cannot be crowdsourced to amateurs. It has to be done professionally by an experienced in-house team. Unfortunately, that team, along with its vast knowledge and experience is long gone. It is unclear how Microsoft is going to rebuild such a team.

So, what does this mean for Microsoft’s long-term future?

Eight years ago, I explained why the iPad, which was just a half-baked computer back then, became a roaring success

But what about the PC? In the pre-iPad era, PCs are seen as slow, unreliable and frustrating piece of contraption. Most of the time it works okay, but it often has the habit of stymieing what you are currently doing with incomprehensible and unexpected error messages, slow reactions and all sorts of technical excuses on why it can’t complete what you command it to do. Why can’t the PC work as instantaneously and reliably as everyday home appliances? Why do you have to often wait for the PC to do seemingly trivial tasks when it is supposed to be able to perform calculations millions of times faster than any human? Unfortunately, most consumers never ask this question because it has become the accepted order of things. They have come to accept that computers are that way.

Then one day, Apple came up with the iPhone followed by the iPad. Suddenly, consumers realised that a parallel universe exists where computers actually work, behave reliably and respond instantaneously. No more surprises, stuffs ups, excuses, freezes and wait. In fact, computers were no longer computers—they had become appliances. Once consumers got used to this parallel universe, there’s no going back to world of unreliable and unresponsive computers that don’t always work. 

Since then, Microsoft missed the boat. Today, they are no longer relevant in terms of smartphones, tablets, smartwatches and other consumer electronic devices. They still have a huge commanding market share in traditional computers. Even till today, Macs still command a distant second place in terms of market share.

But since then, after missing the boat, Microsoft had learnt a lesson. They cannot continue to produce operating systems that cause PCs to gain the reputation of unreliability. In contrast, Apple’s Mac has a reputation of creating computers that “just works”. In a sense, Apple provided the much-needed competition to force Microsoft to make great products.

Stranglehold In The Corporate Market

In the corporate market, Microsoft still commands a stranglehold. They still have not yet abandon Windows for macOS en masse.

Why? The reason is very simple.

The corporate market is extremely conservative. They need to maintain backward compatibility of their existing systems. Their existing software needs to work. They cannot and will not allow anything to get in the way of disrupting continuity. That explains why there are still holdouts in the corporate still clinging on to Windows 7. In general, corporates are loathed to try out the latest updates of Windows. Every update has to be tested by their IT department before being allowed to be deployed to the rest of the organisation.

In view of corporate conservativeness, Microsoft expended great effort to make sure that Windows maintains backward compatibility with old technologies. Software and hardware that works with Windows today will most likely continue to work in future versions of Windows for the foreseeable future.

However, the price of maintaining backward compatibility is increasing complexity. Increasing complexity means increased difficulty in testing. It is at this point that Microsoft decided to make the bond-headed decision to crowd-source testing to amateurs. This is the situation that Microsoft finds itself today.

Back to the bad old days

Today, Microsoft is regaining its old reputation of producing unreliable, undependable, defect-prone and inferior software. Their Windows 10 is giving their users such a horrible experience by disrupting their lives with defects, errors and in some outrageous cases, loss of data.

Contrast that with the experience that they can get by moving to Google (Android and Chromebook), Apple (iOS, iPadOS and macOS) and Linux. Both platforms have matured, with a huge ecosystem of software and tools- even Microsoft’s venerable Office applications run under these platforms. Most importantly, the alternatives are reliable. They can be depended upon.

In a sense, Microsoft is returning back to the 2012 future. This time, there is a crucial difference. The competition (Google, Apple and Linux) has matured tremendously. They have become viable alternatives. They have also nailed the basics right and can focus on new features and innovation. Microsoft, on the other hand, has to return to the basics of getting their own house in order first. If they try to innovate and add features, they risk introducing new breakages to Windows 10.

We can be sure that for the consumer market, the next stage of exodus away from Windows 10 will begin.

How will the corporate market react?

The corporate market is extremely conservative. They hate to rock the boat and risk introducing disruption. They hate change. That is why they rather stick with the devil they know than to switch to the better and more innovative alternatives.

But Microsoft’s repeated screw-ups with Windows 10 is rocking the boat. Their very conservativeness has become counter-productive. By sticking with Windows 10, disruption and unreliability are coming their way anyway. Each software defect chip away their very last reason for sticking with Microsoft.

No doubt, the executive boardrooms of Google and Apple are now probably strategising ways to help the corporate market transition to their respective platforms. The executive boardrooms of the corporate market are also busy examining the alternatives, including Linux. As far as I know, one prominent person from the corporate market, Leo Laporte from Twit TV has already switched to Linux because of Microsoft’s incompetence.

My Personal Experience

I had been very lucky for quite a while. I did not experience any loss of documents in the disastrous October 2018 Feature Update. I had no problems with each update since then. But I knew that it is only a matter of time before my luck runs out.

Indeed, my luck ran out in the May 2020 Feature Update. After the update, I could no longer access my network share and OneDrive folders. Any attempts to do so will result in the application freezing. My macOS, iPadOS and iOS platforms had no problems accessing my network share and OneDrive folders.

On my other Windows 10 computer, Microsoft forcibly updates the Edge web-browser to the new Chromium-based one. But after the update, the sound was not working in websites. I had to download the Firefox web browser to get the sound working on websites.

I was finally disrupted.

Therefore, I have decided to completely switch from Windows 10 to macOS. Time is precious. I do not want to waste time by fixing or finding workarounds to operating system bugs. macOS is a mature alternative that “just works”. I have no time to waste by fiddling with Windows 10. I have no wish to waste my life away with frustration. I must move on.

What you should seriously consider

You may be lucky so far. But make no mistake. Your luck will run out eventually. If you rely on Windows 10, disruption will come your way eventually. In the worst-case scenario, disaster may happen instead. You may lose everything.

If you are using the Home edition of Windows 10, you do not have any choice in deferring operating system updates indefinitely. With each update, there is always the possibility of disruption at best, and disaster at worst.

Therefore, now is the time for you to plan for a transition away from Windows 10.

About the author

I am a Technology Consultant, whose passion is to help small businesses reach their full potential through mastery of digital technologies, strategies and marketing.