There was a time when Windows was cool. A long time ago, people lined up to get new versions of Windows when they went on sale. Maybe not quite the numbers of people outside of Apple stores at the height of iPhone madness, but still – Microsoft was pretty cool.

When the iPhone was released in 2007, Microsoft began its long decline with consumers. Today Microsoft is a modern-day IBM – important to enterprises but painfully unhip for consumers, shipping products that some of us need but few of us love.

It’s a sad story of bad timing, self-inflicted wounds, poor products, technical and marketing snafus, and eventually downright consumer-hostile moves born of desperation.

The interesting thing about this list is that you will undoubtedly have your own examples of Microsoft misses that I don’t mention. But you’ll probably be hard-pressed to come up with successes that have endeared Microsoft to your heart in the last ten years. It’s the cumulative effect of these moves that have taken Microsoft out of the consumer market.

Sadly, it doesn’t matter very much to us that Microsoft is no longer a strong consumer company. Since Microsoft is positioned to be a very successful enterprise company, why does it keep trying to win us back?

Vox put it this way.

“Consumer sales aren’t very important to Microsoft’s bottom line, and that has been true for years. The modern Microsoft is fundamentally an enterprise software company. It sells copies of Windows and Office to businesses, along with online services and technical support contracts. It’s a lucrative and stable business that could generate healthy profits for the Redmond software giant for decades to come.

“But it’s hard for a company that was once at the forefront of consumer technology to accept a future making profitable but obscure products for businesses. It’s a lot more glamorous to compete with Google and Apple than IBM and Oracle. So Microsoft keeps trying to boost its consumer profile, with little success, while the company’s revenues and profits come disproportionately from lucrative but unglamorous business customers.”

Here’s how Microsoft became uncool.

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Bad timing

Windows Phone  Microsoft was caught flatfooted by the success of iPhones and Android phones. By the time it came out with a plausibly competitive operating system, Windows Phone, the Apple and Google app stores were thriving and both consumers and developers had committed to them. Microsoft couldn’t attract interest from anywhere – not from carriers, which ignored Windows phones; not from developers, who saw no reason to develop for a third platform that appeared to have little chance of being profitable for them; and not from consumers, who were entranced by the shiny new Apple and Samsung phones.

Everything important about Microsoft’s decline with consumers started here. Without its own devices, Microsoft could not leverage any synergy with Windows computers or its other services. That continues to this day, as Microsoft is shut out of the market for home assistants because Cortana isn’t drawing any attention. The nature of consumer products today is that almost nothing will be successful unless it is the default on a mobile device.

Schools  When Google started working on ChromeOS, it should have been possible for Microsoft to look forward and see that schools would be attracted to an OS that would run well on cheaper hardware than Windows requires. True device independence means that Chromebooks are far easier than Windows laptops to maintain and pass between students. Microsoft’s long-delayed response with Windows 10 S was – well, let’s be charitable and say it was unconvincing. It’s probably too late now. The effects of that are already being felt as a generation of kids comes out of school deep in Google’s ecosystem, with no loyalty to Windows.

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Self-inflicted wounds

Windows failures  Windows Vista was released a few months before the iPhone. Vista was a hurry-up job cobbled together after internal work on a more advanced version of Windows collapsed. Vista was a solid OS but computer manufacturers sold underpowered computers that could not run Vista well, so most people’s first experiences with Vista were frustrating. Manufacturers were also slow to release driver updates, leading to persistent device failures and crashes. It was Microsoft’s job to have pushed the manufacturers to improve our experiences with Vista. Instead the word of mouth killed Vista; people began to learn the habit of postponing computer purchases, and Microsoft had to rush Windows 7 out and try to bury Vista as if it never existed.

But nothing compared to the Windows 8 debacle. Microsoft followed exec Steven Sinofsky’s vision of a new UI that would look similar on desktop computers and mobile devices: the synergy would make everyone happy, see, because the new UI was super-cool and we’d love the consistency and we’d demand Windows Phones so everything would interact.

Every bit of that was wrong. We hated the UI, no one cared about consistency between phones and computers, and the interaction between computers and Windows Phones was weak. Microsoft lost a lot of trust and loyalty to that misguided Windows 8 Start screen.

Windows updates  I hate installing Windows updates. You hate installing Windows updates. Everybody hates installing Windows updates. Almost everyone has had the experience of seeing the dreaded message “Do not turn off your computer” and the endless swirling circle at the worst possible time. We trust updates on our mobile phones to go smoothly and not muck things up. We don’t trust Microsoft to update Windows without causing problems.

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Poor products

Microsoft has been trying to rekindle consumer enthusiasm with new hardware, new programs, and new Windows features. Each and every one has gone nowhere, either ignored or actively disliked. A few of the misfires:

  •    Windows app store  Microsoft dreams of a world where we embrace a new generation of Windows programs. If we would just give up our old-fashioned desktop programs (in other words, everything you consider to be a “Windows program”), well, Microsoft is just sure that Windows would run more smoothly and be more secure and updates would happen more smoothly and, and, gosh darn it, why don’t we just listen? Because so far we don’t care. Most people aren’t even aware that Windows 10 has an app store. If you go look at the store, you’ll find there’s just a bunch of junk and certainly nothing essential. It doesn’t help that even Microsoft’s own efforts to create programs for the app store are none too compelling. Since consumers aren’t paying any attention to the app store, developers are ignoring it as well – a vicious circle with no easy way out.

  •   Bing  Microsoft’s answer to the Google search index has fallen flat with consumers. Microsoft uses the underlying technology in some of its business products but Bing falls further behind Google every day in search accuracy and consumer interest. Do you use Bing? Of course not. Who would?

  •   Cortana  Poor Cortana! Seldom used, ineffective, ignored by developers who are eagerly creating products and services to work with Alexa (Amazon Echo), Google Assistant, and even Siri. And we will never use Cortana because she’s a pain to reach on our phones and home assistants compared to using the default for each device.

  •   Edge  When Internet Explorer began to lose ground to Google Chrome, Microsoft decided to jettison the aging program and start from scratch with Edge, a new web browser. It used a similar E icon, to make sure consumers were confused, and created a new programming environment for extensions, the add-ons that make a browser more useful, thereby guaranteeing that developers would ignore Edge and we would stick with Chrome. Edge is slowly being improved and in a couple of years might catch up with where Chrome is today. We still won’t use it.

  •   Media  Microsoft killed the Groove music service a couple of months ago, pretty well ending Microsoft’s long-held ambition to play a role in the media world. Microsoft has had no success in any of those attempts. Microsoft attempted to get into the living room by having us set up computers running Windows Media Center with our TVs. That didn’t go well. Microsoft’s competitor to the iPod, Zune, became a punch line because it sold so poorly. At one time or another Microsoft has tried to sell video and music, either as downloads or streaming services. All of them failed miserably when no one paid attention.

  •   Microsoft Band  Remember when Microsoft tried to compete with Fitbit with a health band for measuring footsteps? Like many of Microsoft’s efforts, there was nothing wrong with it, but nothing particularly right, either. No spark, no magic, no sales.

  •   Home assistant  The new market for home assistants is heating up: Amazon sells millions of Echos, and Google is making a strong effort to catch up with Google Home. Cortana can’t compete. At one time Microsoft intended to partner with lots of companies to produce Cortana-powered speakers but that project disappeared without a trace. Well, one trace, an overpriced Harmon Kardon speaker that must have been required to fulfill some contractual obligation. Certainly no one was asking for it and no one has bought it.

  •   Hololens and virtual reality  These are early days for augmented reality and virtual reality and so far almost everyone is flailing, unable to come up with a compelling reason for us to spend hundreds of dollars on gear that is finicky and not very interesting yet. Microsoft has been working on Hololens for what seems like forever. It’s a visor with clear lenses that superimposes information and objects on top of the real world. There are exciting possibilities but Microsoft is a long way from conquering the technical problems and hasn’t even tried to make it a consumer product. Instead Microsoft is working on a different platform, currently named “Windows Mixed Reality.” In typical Microsoft fashion, the name is confusing; it appears not at all to be “mixed reality” but rather plain vanilla virtual reality. There is less support for it than the more interesting competitors – Sony Playstation VR, HTC Vive, and Oculus Rift. Within a few months, prices on Windows Mixed Reality headsets were being drastically discounted by 40-50%, which still wasn’t generating any sales.

  •   Paint 3D  Microsoft has been trying hard to think of something new for Windows that will make you happy. Example: last year it pushed out Paint 3D, a lightweight app for creating 3D objects, something no one wants to do. It managed to irritate lots of people by announcing that the new program would replace the venerable original Paint program, which a fair number of people still use as a familiar friend. It backed away and kept MS Paint alive due to an “incredible outpouring of support and nostalgia,” meaning it was forced again to placate all the people it had pissed off. Other new features have been added to Windows 10 in the last couple of years that have come and gone without a trace.

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Technical and marketing snafus

Since I work mostly with small businesses, I’m particularly sensitized to the confusion that Microsoft has created with its dual systems for logging into Microsoft services. Poor branding and inconsistent descriptions make it impossible for non-technical people to know if they’re using a service with their “personal” or “work or school” accounts.

OneDrive  The account confusion is one reason that OneDrive did not sweep aside Dropbox and other competitors. Microsoft then compounded the confusion by branding a different service as “OneDrive for Business,” which sounds harmless until you realize it has an identical interface – literally, you can’t tell the two apart – and yet they are completely separate, with confusing bits that unexpectedly work differently. (Not to mention that “OneDrive for Business” is not intended to be used for shared business files, but that’s a different kind of screwup.)

Microsoft just introduced a new OneDrive feature for storing files online while accessing them in the familiar File Explorer interface. They managed to implement that so poorly that even technical people are confused, and normal consumers have no idea it exists and couldn’t understand it if they knew.

Skype  At one time Skype was on its way to being the default platform for casual global communication. Microsoft bought Skype and perhaps by coincidence things started going sideways. There was an extended period of confusion about how to log into Skype – a Skype ID? A personal Microsoft account? Both? Then the Skype team began a long project to change the program’s underlying architecture, resulting in years of poor call and video quality. During that time Microsoft began to muck around with the program, changing the interface, trying to push people to a new, unlikable version in the app store with a cartoonish look and fewer features, then bailing out and pushing back to the desktop version. People have fled to apps that work better on their phones.

Oh, and to add insult to injury, Microsoft deeply injured the brand when it renamed its enterprise program “Skype for Business,” even though it had nothing to do with Skype. Users were then thrown into the same confusion between personal and business accounts, unsure what credentials to use and unsure whether a reference to Skype in a Microsoft program referred to something they used or not.

Skype is still widely used but it has nothing like the influence it could have had.

Surface  The Surface devices were influential and well designed. In time competitors came out with similar devices with detachable keyboards and as time passed many of us circled back to traditional laptops. Microsoft has now lost its way with Surface. Premium laptops are the bright spot in the computer market but Surface devices are invisible, too expensive and saddled with dated technology that has not been refreshed  for too long. Last year Microsoft introduced the Surface Laptop, a perfectly nice thin and light premium laptop, but it has sunk without a trace, generating no interest and no sales – too expensive and lacking in features compared to competitors. The Surface division is probably profitable for Microsoft but no one would be surprised if Microsoft bailed out.

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Consumer-hostile moves borne of desperation

Microsoft’s desperation to shake money out of consumers for Windows has led it down some dark paths.

Advertisements and crapware  Every time you see a popup pushing you to use OneDrive, you’re looking at an advertisement. That’s all it is, just an ad. Windows is full of them now. Those panels in File Explorer about OneDrive, or suggesting that you subscribe to Office 365? Just ads. When you change the default web browser in Windows 10 from Edge to Chrome, a popup will try to change your mind. It’s an ad.

But it’s worse than that. The Windows 10 Start menu is disgraceful. All those game tiles are ads, Candy Crush and Bubble Witch and Mickey Mouse and all the rest. It’s pretty gross.

Overly aggressive upgrade push  Microsoft was sad and disappointed that the entire world did not leap to upgrade to Windows 10. It began desperate attempts to force us to upgrade, which started off as annoying reminders and eventually led to outright deception. This was a particularly dark chapter in Microsoft’s relations with consumers.

Windows 10 S  Microsoft has created a version of Windows that cannot run any program you believe to be a “Windows program.” This new version of the OS has no advantage to you. Oh, sure, if the whole world was transformed to it overnight and all our programs were rewritten, Windows would run slightly better. That ain’t gonna happen. It’s a pipe dream and I honestly cannot imagine why Microsoft is promoting it. But if you buy a Surface laptop, your first experience will be when you discover that you can’t install any programs on it, something that will not have been communicated clearly. You’ll have to do an upgrade to the operating system before you have a functional laptop. It’s not hard to do that, but putting you through that exercise reeks of desperation.

Oh, and that “better” version of Windows can only run the Edge browser, and will only use Bing as the engine for web searches, because Microsoft hates us.

That’s our laundry list of Microsoft’s failures with consumers. Let’s add three quick footnotes.

  •   It’s only fair to note that the Xbox is a successful gaming console. It’s Microsoft’s only successful consumer product. Let’s call it the exception that proves the rule.

  •   Windows 10 is the best computer operating system on the market. It keeps getting better, despite the annoyances. Remember: you will use a Windows PC to do your work for the foreseeable future.

  •   Apple has given up on the computer market. Don’t be fooled into thinking that the grass is greener on the other side.