2024 Winds Down with a Fresh Look at the Microsoft Client Stack (Premium)

Microsoft’s strategy for moving customers to new versions of its client software products involves two distinctly different–one might say, incompatible–tactics. The first is the traditional customer-focused meeting of needs that dates back to the company’s founding and is the one I suspect most Microsoft employees conjure when asked about their work. But the second tactic is perhaps more familiar these days. Using dark patterns, anti-competitive in-box behaviors, and other means, Microsoft has enshittified its products to make them conform to some broader corporate strategy.

The result is confusing. But it’s also not all that uncommon in personal technology. We’re all familiar, if vaguely, with the privacy trade-offs we make to gain the advances in Google services like Search, Maps, and Photos, for example. We know that we sacrifice some openness and eliminate choices when we buy into the Apple ecosystem so we can enjoy the “it just works” nature of the company’s cross-device integrations. And everyone is perhaps a bit too familiar with the notion that “if you don’t pay for the product, then you are the product,” without really understanding the implications of the resulting shift to an advertising-focused model for most of the products and services we use every day.

What may be less obvious is that Microsoft, observing these tactics from the outside and over a period that is nearing decades, collectively wondered, “why aren’t we doing that?” Microsoft was hobbled by two massive antitrust cases in the late 1990s and early 2000s, and it was that hobbling that lead to the creation of today’s personal computing market, with multiple companies–Amazon, Apple, Google, and Meta among them–now abusing audiences that are much larger than any Microsoft ruled over 20 years ago. If they can do this, why can’t Microsoft? After all, it has the resources, the smarts, the cloud infrastructure to compete with the biggest and the best.

And so it has.

We all know that Windows shifted to a cloud-like updating model, Windows as a Service, with Windows 10, and that this system has been made even more terrible in Windows 11, and is now called “continuous innovation.” We know that Microsoft quietly changed how Default apps works in Windows 11 and how it now pushes users to Microsoft Edge, even when they have taken the time to configure and use another browser. We know that the new Outlook displays ads that look like email messages if you don’t pay for the product, and that that might the least of its problems. We know that OneDrive Folder Backup is silently enabled when you sign in to Windows 11 Home for the first time, and that it will often be enabled for you on Pro, too, even after you’ve declined the request several times. And we know that Windows 11 tracks your activities, is bundled with crapware, has advertising all over the place to cajole you into using Microsoft products, services, and preferred configurations, and that those advertisements use a combination of intimidation and falsehoods–dark patterns–to convince you do things its way.

And yet we use Windows. Incredible.

Or not so incredible. This past year, I’ve latched onto a concept that isn’t new but was forgotten, that there are in effect two sides to each of these products, and thus to Microsoft, I guess. There’s the side that’s solving hard computer science problems and meeting customer needs. And there’s the side that is only interested in pushing Microsoft’s revenues up ever higher and is willing to make that happen at the expense of its customers. I even spoke about this dichotomy, at the only industry event I spoke at this past year, and in doing so, I ended providing a follow-up to a talk Mary Jo gave a year earlier, in which she discussed “where Microsoft’s needs and the needs of its customers diverge.” This is the knife edge we all live on as Microsoft customers. And we have some choices to make.

Perhaps not surprisingly, I often focus on the negative side of this equation. Not for hits, whatever that means, or to complain per se, or not only to complain. But because I have a long-held belief in the power of relationships, and that all healthy relationships are win-wins. In Microsoft’s case, this means that we get what we pay for, and it works out for both sides. This was the traditional equation. And then it wasn’t. At least not always.

But relationships are also complex. There’s no such thing as two people always agreeing, for example, and no matter how strong your relationship with a spouse, sibling, parent, or other family member or friend, you’ve been at odds. This reality means that we all compromise, every day, silently and unconsciously calculating the relative value of each relationship. When it skews too far in one direction, it’s over. But if it’s a net positive, it persists and maybe even thrives. My wife can’t be on time to save her life, but my existence would be borderline pointless without her because of the many, many things she gets right. So I will bite my tongue as I obsessively keep checking the time. It’s the little things.

We all know that Microsoft evolved over time, expanding past MS-DOS and then Windows into apps and then suites (Office), to workgroup servers (NT), to enterprise servers (Windows Server) and infrastructure, and then to the cloud (Azure, Microsoft 365). We know that in doing so, it became bigger, and more successful and diverse. (We know and will ignore that it also failed with many more products and services, many consumer-focused, as well. Moving on.) And that during this evolution, Microsoft went from being the Windows company to being “Windows first” to being “Windows best” and then to … whatever it is today. A company in which Windows is important, sure, but also not the focus let alone the center. And we all know the result on product quality, as I glossed over earlier in this article.

But as I’ve noted recently, there is that other side. And when people suggest to me or even assume that I’d be using a Mac, or perhaps a Chromebook or Linux, and not Windows if I weren’t somehow wrapped up professionally in this whole Windows thing … I pause. That’s never been true, I have long preferred Windows to the competition and for all kinds of reasons. But it’s fair to say that I’ve also always been fascinated by that competition, and that some of my earliest memories of my professional life involve downloading and creating installation floppies for Slackware Linux in the mid-1990s and buying an iBook in 2001 so I could test the first version of Mac OS X. I am curious about these things, always have been.

And yet here I am. And once again, I feel oddly compelled to explain that, yes, I really do still prefer Windows, and that that’s true despite all the issues of recent years. But my remarks about relationships above provide the context for why that’s so: There is plenty of bad, yes, but the good still outweighs the bad. There is also this related side story about the broader industry shift to mobile devices that occurred over the past 15+ years, where we have collectively come to rely on Windows and the PC less and less. This is easily seen as a negative, but in this, I do see the positive, too: Because I read, watch videos, engage on social media, and do other “consumption” and entertainment activities on other devices, my PC is freed up to perform the tasks for which it is most optimal. Key among them what I think of as now-traditional productivity tasks, most especially writing, which is my real focus. And for that, Windows is best. For me.

So that one is easy and even straightforward. I’m open to the alternatives, test and use them routinely, even. But I always come back to Windows.

What about the rest?

Microsoft offers a stunning array of functionality via Microsoft 365, a subscription I pay for twice–one consumer-based, one commercial–key among them the Microsoft Office suite of productivity apps and OneDrive with its cloud storage. And it’s fair to say that my usage of these things has declined, though it’s also fair to say that I do still use them every day. I shifted to Google Drive last year when the OneDrive terribleness became too much to bear, and my primary writing apps are both Markdown-based and much simpler and lighter than Microsoft Word. But here I am an outlier. For most people, most mainstream users, certainly, Office and OneDrive, and the integration that Microsoft provides with these things in Windows, is obvious.

But this past year has been interesting. In part because I write and update the Windows 11 Field Guide, and in part because I engage in this kind of testing all the time, I’ve used Microsoft Edge and the new Microsoft Outlook quite a bit. On the book front, I need to update the non-several chapters of Edge content once or twice a year–that product is updated even more frequently than Windows itself–and the new Outlook is, well, new, and will replace Mail and Calendar in less than three weeks. So it needs a new chapter.

Both of these products live in a moat of negativity. For Edge, it’s all about the forced usage, the way that Windows quietly launches this product in certain circumstances and ignores the explicit browser choices that the user made, a situation I find unbearable and wrong. Outlook is a little different, though. This one sits at the nexus of a problem I’ve been meaning to write about, where the most expert technical users reject something new, usually by highlighting esoteric minor missing features. It’s what we see now with Windows 11 on Arm, as if the lack of a single thing that most people do not need somehow undermines the entire platform. I don’t like this, and I struggle with it. But it’s particularly acute with Outlook. There’s a kind of “I’ll give up classic Outlook when you pry it from my cold, dead hands” mentality that I have trouble understanding. Because classic Outlook, objectively, is f#$king terribly.

Please don’t take that as an invitation to argue otherwise or to relay that one missing feature for the upteenth time. I don’t care, I’m just tired of it. And more to the point, having switched to a web interface for email many, many years ago–Gmail in my case, but I’d be OK with Outlook.com as well–I don’t even understand the need for an Outlook client app, at least on the desktop. It’s not just old-fashioned, it’s pointless.

But it’s not pointless, because corporations are old-fashioned and change averse, and they use Outlook, and they are not changing. And so Microsoft was forced to make some hard decisions with Outlook, a program that dates back a personal information manager from the 1990s and whose first foray into email, as Outlook, was the most incompatible and stupid version of email ever created. The decision it made seems to please no one. As it is doing with the rest of Office on the desktop, it first moved the Outlook add-in infrastructure to be web-based. And now it is making the new Outlook using these same technologies. This makes sense to me, in the context of even doing this work, because classic Outlook is a nightmare of old, insecure code. But my God do people hate it.

But here’s the thing. In using Edge and the new Outlook this past year, most especially over the past few months, I’m struck by how inoffensive both can be. Not by how inoffensive they are, mind you. There are offenses. But in both cases, I’m coming around to the notion that the relationship mix in both is positive. This still surprises me a little bit.

To me, Microsoft Edge is poorly architected, meaning that it’s loaded down with features I don’t want and won’t use, and I would prefer for most of those things to be implemented as extensions that I could enable (or not) when I first set up the product (or later, as needed). You can turn off many of these features, thankfully, but Edge will not remember this configuration, for obvious reasons: When I sign in on a new PC, and I do that dozens of times per year, it’s mostly back to the default configuration again.

Leaving aside that problem–which dogs Microsoft Office, too, by the way, in that there’s a settings sync feature that is woefully incomplete–I have noticed that when you strip Edge of unwanted features, it can feel lightweight and minimalistic. You can get rid of all the silly Workspace and tab features, remove the Copilot icon and not use the sidebar, and it’s fine. (Well, it’s fine if you use the right tracking and ad-blocking extensions, let’s not forget that.) There are even some nice customization features I like, include the color and AI themes, and I’ve always liked the Edge font/UX aesthetic and how it looks natural in Windows 11 and, as important, correctly sizes with the display scaling. That’s nice.

But there’s more. Back in May, Microsoft revealed that it was rewriting key parts of the Edge user interface to make the app more responsive. And this has resulted in an astonishing and noticeable perceived performance improvement. I still don’t like that Edge implements things like History (Ctrl + H) and Downloads (Ctrl + J) as pop-up windows, but part of that is that these things always took so long to appear and draw. But now they are lightning-quick: Thanks to the underlying changes Microsoft is still making–this work is apparently continuing into next year as more UI bits are upgraded–Edge, suddenly, is really fast. You can see this for yourself: Try those keyboard shortcuts above and see how fast those windows open. Or open Browser Essentials from the “Settings and more” (“…”) menu: It appears so fast you can almost hear a cracking sound. It’s pretty impressive.

Are these changes enough to … gasp .. make me switch (back) to Edge? I’m not certain, honestly. But I’ve found myself prolonging my time with Edge in ways I never did before. This is a positive sign for a product I’ve been quite disdainful of for a long time. It’s unexpected.

As for Outlook, I’ve never understood the hate. Unlike with Edge, there is no chance I’m switching at all, web-based email is just too efficient for me to bother. (I use mobile Gmail on my phones.) But with one exception, I’ve found the new Outlook to be nothing short of excellent. The personalization features, in particular, are off the charts.

The one exception, and it’s vaguely defensible, is that if you configure the new Outlook without using a paid Microsoft 365 account–consumer or commercial–it displays ads. And those ads masquerade as new email messages, which is a form of dark pattern I am not OK with. This means that I cannot just configure the new Outlook with my Gmail (really Workspace) account. I must also configure it with my Microsoft account, and then make sure Gmail is the default. And when I do that, it works fine. No ads.

This is a great-looking app. It works well, runs quickly, and does everything I need. And more. It’s incredible how much Microsoft packed into this thing. And yet, we’ll be dealing with the hate for years to come. Microsoft will make the new Outlook opt-out for smaller businesses in early 2025 and then for bigger businesses in 2026. And this elongated schedule, which is curiously customer-centric, given the world today, guarantees that the haters will have multiple chances to pop-up, mole-like, every time there’s news, so they can express their disdain for this thing. I don’t get it.

The other day, someone on social media somewhere, responding to my editorial about the end of Intel and x86 suggested in a non-question question that my reliance on Microsoft client products had come to an end. That’s not the case at all–I continue to use those things that are best for me, as we all should–but there has been an interesting shift recently, and not in the direction that person expected. Left unsaid in all the talk about me testing things and choosing appropriately is that Microsoft can win me back. That might be happening with Edge, for example. It could absolutely happen with OneDrive. And if I were concerned with client email apps, it would happen with the new Outlook too. Is Loop off the table because I love Notion? Not at all. The bar there is high, to be fair. But nothing is permanent.

And maybe that’s the point. Microsoft wouldn’t have to do that much to reset our relationships with its products and services. I feel like the changes it made to Recall provide an obvious guide for how that could work: Make optional things opt-in, not opt-out. Don’t screw around behind our backs and make decisions for us that are contrary to our explicit choices. Stop badgering us to do things in a way that is better for you but contrary to our needs. Allow us to customize things so they work well for us. Basically, treat us like the customers we are. And if we’re paying for the thing, for crying out loud, Microsoft, back off.

This all feels like common sense to me. And while there is so much terrible out there in this space, I also see some signs–small signs, for sure–of a correction. I welcome any positive change.