
Several years ago, I was working on the Programming Windows series that I later turned into the book Windows Everywhere. As I progressed through that history, I started collecting themes, or ideas, that might define specific eras. And one I remember distinctly was the notion that Rapid Application Development (RAD) environments like Visual Basic enabled a new style of programming in which you would spend more of your time creating an app’s user interface and would only need to write a minimal amount of software code.
Like so many bad ideas, this one was dangerous specifically because it felt true. And without getting into the technical details of why this is so, I’ll just say that, leaving aside the simplest and least professional of classic VB apps from 30 years ago, I was wrong on that point, And that I’ve spent the past several years in what might reasonably be described as a manic push to prove myself wrong again and again.
In the unlikely case that you don’t know what I mean by that, I am referring to .NETpad (pronounced “dot net pad”), my partial clone of the application Notepad that Microsoft has bundled with Windows since the beginning (and beyond, as its immediate predecessor was written for MS-DOS). I have created what now feels like an uncountable number of .NETpad versions in various programming languages and application frameworks. As such, I am in some ways more knowledgeable about Notepad and its capabilities than almost anyone.
A lot of that knowledge has come from failure.
You are of course familiar with the famous John F. Kennedy quote, “We do these things not because they are easy, but because they are hard.” I’m not that inspirational: I started copying Notepad specifically because I believed what many still believe today, that this is a simple app and it would be easy to copy as I learned each of the .NET-era frameworks, in turn, while writing that series that became a book.
During this years-long process, I came to really respect Notepad. It’s a deceptively powerful app, full of little features loved by those who know it well, but also approachable to beginners and minimalist. I also maybe got a little caught up in my own successes: I was surprised by how much of Notepad’s functionality I could replicate, and while I never got to 100 percent of its feature set, I did add features that Notepad didn’t have (some of which Microsoft later added, like text zoom).
The problem with Notepad until fairly recently was that it was technically old-fashioned. It was a classic Win32 desktop app because it came out of an era in which that was a developer’s only real option. It was updated only sporadically during its first 20 years, at first because there was little reason to do so, and then increasingly because its code base was so out of date. The move to Unicode with Windows NT in the 1990s was particularly problematic, with Unicode-related issues popping up again and again over the intervening years.
Making NT itself fully Unicode enabled took several years–it wasn’t until Windows 2000 that all languages worldwide were supported by the base OS–but during this time Notepad took on an outsized role because it had to deal with all the different encoding formats that Unicode-based text files can use. And that was as true in the early days, when POSIX compatibility was considered key to the platform, as it is today for Linux interoperability via WSL. Indeed, Notepad’s support for Unicode encoding formats is so extensive and ill-understood that it’s almost black magic. It’s one of the Notepad features I have never cloned, even partially.
Notepad was one of several in-box apps that were cleaned up during the development of Windows Vista, but whatever improvements Microsoft made to the app were mostly low-level and went unnoticed by mainstream users. The focus of Notepad’s updates shifted over time from admins and IT pros to developers as Microsoft sought to stem the defection of that latter audience to the Mac and Linux. But with Windows 10, Microsoft began emphasizing end user features too–improving find/replace, adding text zooming, and so on–and it was eventually added to the Microsoft Store so that it could be updated more easily. And more frequently: That process has accelerated dramatically in Windows 11.
Ah, yes. Windows 11.
As everyone knows, Windows 11 introduced a simpler new user interface based on WinUI 3, and Microsoft began updating, replacing, or obsoleting the system’s in-box apps based on telemetry and need. Some of these changes were controversial, as was its pretty but dumbed-down UI, especially in the initial release. This is when the term enshittification entered the conversation. Some seem to dislike this term for what I feel are prudish reasons. But it’s perfect because it’s concise and immediately understandable. And once you understand that it exists, you start to see it everywhere.
Oddly, enshittification is also misunderstood. For example, some will apply this term when a company adds a feature or change to a product or service they don’t like. But that’s not enshittification, it’s a subjective opinion, a preference. Enshittification occurs when a company changes a product or service to benefit itself–strategically, financially, or whatever–while knowing full well that this change will harm its users. And so when we see a change to some product or service, it’s important to consider the intent. Why was that change made? Is it malicious, or just different?
I focus largely on Windows, as you know, and so I pay careful attention to any change that Microsoft makes to this platform. (And these days, those changes come in such a rapid-fire cadence that it’s next to impossible to keep up. That, itself, may be a strategy to disorient the customer base. But I’m getting off track.) And so last year, I documented the changes in Windows 11 that, I felt, were examples of enshittification–forced telemetry, preinstalled crapware, constant feature updates, forced Microsoft account sign-ins, forced Microsoft Edge usage, arbitrary hardware requirements to force PC upgrades, OneDrive forced feature usage, and other bad behaviors–and then assigned each a severity level. I also documented workarounds and fixes, since identifying the problem is only the first step on the road to recovery.
No one uses Windows to use Windows, as the saying goes, they use Windows to access the apps and services they need. And, yeah, sort of. But like the bad idea I noted above, this isn’t as true as it seems.
When I don’t use Windows–if I’m using a Mac, a Chromebook, or Linux, and even sometimes a mobile device like an iPad–I miss features from Windows that aren’t available elsewhere. For example, I made the case that macOS multitasking is inconsistent and broken, because it is, and then I documented how you can correct that to make it work more like Windows, which is to say consistently and correctly. But there’s a lot more. And to bring this back on-topic, there are two Windows in-box apps I use every single day, too. And I miss them when they’re not available.
Those apps are Paint and Notepad.
These are two of the oldest apps in the Windows ecosystem, with both dating back to the 1980s. I described above how Notepad was ignored by Microsoft for so many years, but Paint was treated even more shabbily. Microsoft tried to replace it in Windows 10 with a terrible app called Paint 3D. It reversed course on that mistake, thankfully, but by the time Windows 11 came around, Microsoft began the difficult process of updating, replacing, or obsoleting the system’s in-box apps, as noted above. These two apps were deemed important enough that they would be updated, but their codebases are so old that doing so would be difficult. And so they underwent a process called modernization by which their front-end user interfaces were replaced with new WinUI 3-based fascias.
This process ruined Paint, at first. The initial modernization work appeared to be done by interns who had never used Paint and didn’t seem to understand Windows. The ribbon UI from the classic app was replaced by a pseudo-ribbon that could not (and still can’t be) collapsed. It only supported Light mode, which looked like a spotlight at night when used in Dark mode. And the app killed its most common keyboard shortcuts, killing in turn its users’ muscle memory. It was a disaster, a far worse fate than Microsoft simply ignoring the app.
Amazingly, Microsoft turned things around. It took a few years–yes, really–but most of the issues I note above were corrected in time. Today, Paint is better than it ever was while respecting the workflows its users expect. This is precisely what app modernization should accomplish. It just shouldn’t take that long or involve so many mistakes.
Notepad’s modernization went much more smoothly. Microsoft added a fresh Windows 11-style user interface that supported Light and Dark modes perfectly. And all the classic keyboard shortcuts kept working normally, with no hitches or glitches. Notepad was, I wrote, “an example of an app refresh done right, a non-disruptive upgrade that actually made the app better.” This was the poster child for app modernization.
And then AI happened.
I suspect that the predictably negative comments I’ve seen from people about the most recent Notepad updates are tied to three things. Many, but especially older, more experienced users, abhor any change to apps they’ve used for a long time and are familiar with. They fear and distrust AI. And they’re tired of the constant churn in Windows, and believe–as I do, actually–that mature legacy platforms like this should be treated with respect and mostly left alone. If it ain’t broken, don’t fix it.
But again. Is this enshittification?
Those who believe so will point to Microsoft’s chaotic introduction of new AI features everywhere in its ecosystem, the over 100 Copilot-branded products and services it now offers, and how these things are either unwanted–tied to my points above–or are at least a form of bloat. But this view is objectively incorrect. Yes, Microsoft’s introduction of AI features is chaotic, and that’s tied to a “bet the company” strategy in which it sees AI has a potential extinction moment if it doesn’t advance past well-established rivals (Google, Amazon) and newer, faster-moving AI startups (OpenAI, Anthropic). But the presence of enshittification also requires the second half of that equation. It has to materially worsen the user experience for customers, and that change has to be purposeful.
And I get it, you may not like AI. You may still for some reason believe it to be a hoax, or at least overblown. But that doesn’t make what Microsoft is doing in Notepad–or in Windows 11, Microsoft 365, or anywhere else–enshittification. That’s just your opinion.
When Windows 11 asks me to enable OneDrive Folder backup and I decline that offer and then it just enables it anyway, that’s enshittification. When Windows 11 adds a Copilot app that changes dramatically over a short period of time, that’s simply chaos. Bad, but not enshittification, and for too many reasons to count. The key reason being that you can simply uninstall the app. And that, to me, is key to this dialogue. How have any of the changes to Notepad impacted anyone negatively? And can those changes be ignored or disabled?
In December 2021, I wrote about my hands-on experience with the then newly-redesigned Notepad for Windows 11. As noted, it was prettier and more in keeping with the Windows 11 look and feel. But crucially, it didn’t lose any functionality from the past. There were modern new interfaces for find/replace and settings, that Light and Dark mode support, a revised menu layout but with all the same commands as before, and the new Zoom text feature. That’s a net gain, a win. (For those interested in such things, Microsoft later explained how it modernized Notepad for Windows 11, too.)
Since then, there have been other major changes–like a native version of the app for Windows 11 on Arm, the tabs-based user interface that I’m currently struggling to copy in .NETpad, session state management (not auto-save, as some call it), and spell checking and autocorrect among them–and then a growing list of generative AI features that include such things as summarize, rewrite, make shorter, make longer, change tone, and change format options. More recently, they’ve started testing a prompt-based writing feature that will generate content for you.
Those features are notable for a few reasons. But each requires a “Copilot subscription”–which can be Microsoft 365 Copilot, Copilot Pro, or Microsoft 365 Home/Personal (account holder only)–and use up “AI credits” that the company doles out on a monthly basis. And each is tied to two major initiatives in this expansion of AI capabilities across the Microsoft ecosystem: They use generative AI features related to text–just as new features in Paint use generative AI features related to images–and they can/will be controlled by future AI agents via App actions.
More to the point, none of these things are mandatory. You can ignore or disable all of them. If all you want if “pure” Notepad with none of the frills–OK, you can’t remove the pretty new UI–then you can do that. This is not enshittification.
But the news last week that Microsoft was adding “lightweight formatting” capabilities to Notepad was somehow the straw that broke the proverbial camel’s back. Many saw this as some insidious internal plot that explains why Microsoft really killed WordPad, when in fact, that app had long before crossed over a line in which its continued bundling in Windows wasn’t just a distraction, it was a security problem. WordPad was a rich text editor, and the app’s user interface was last updated as part of a “Scenic Ribbon” push tied to Windows 7 in 2009. Notepad is not a rich text editor. Notepad is a plain text editor. And this lightweight formatting does not change that.
Part of the problem is Microsoft’s fault: As is so often the case, it didn’t explain this change clearly, instead allowing the news to be conveyed via the Windows Insider blog when the new app version appeared in a specific pre-release Windows 11 build for the first time. This post didn’t explain why Microsoft was adding this functionality to Notepad. Instead, it just noted that customers could use a new formatting toolbar to apply formatting as they typed or selected text, “including bold and italic styling, hyperlinks, and support for simple lists and headings.” And that the lightweight formatting was tied to something called Markdown, a topic most people probably don’t understand.
Markdown is a plain text format. It uses simple, HTML-like formatting tags for headings, text styles, hyperlinks, lists, and so on and was designed specifically so that it is both machine readable–any software that can display plain text is seamlessly compatible with Markdown files–and, crucially, human-readable. Here, for example, is how this article, which I wrote in Markdown, looks in Notepad today.

Wow. That’s really scary, huh? Editors that are specifically Markdown compatible, meaning they understand those tags, as Notepad soon will, can optionally display the text in Markdown files like that. Or they can display in a sort of minimalist, light word processing mode in which you can see the formatting. Here’s that same document in Typora, the Markdown editor that I use. This is also not scary. And this is how the new Notepad will work. (I don’t have it on any of my PCs yet, sorry.)

Many assumed that “lightweight formatting” in Notepad meant rich text, and that this addition meant that Notepad was the new WordPad and thus not Notepad anymore. And those that dub deeper either didn’t understand Markdown or what Microsoft’s really been doing in Notepad to begin with. This is a net gain. A win. If you don’t want it or need it, you can simply ignore it, just like all the other functional changes Microsoft has made to this app.
As to the why of adding Markdown support to Notepad, I can only speculate. But this is an educated guess, and it rings true. (He writes, having just explained why that line of thinking can be dangerous.) Microsoft is actively pushing Windows 11 as the ideal platform for developers, and while that push has evolved dramatically over time, it has led to killer features like Terminal and the Windows Subsystem for Linux (WSL). Just last month, it announced even more new features for developers, like the Windows AI Foundry, native MCP support for AI agents, App actions, a VBS Enclave SDK, and more. And while I use Markdown for writing, this plain text markup language sees its biggest success with developers. It’s what most documentation is written in today, and it’s built in to Visual Studio Code and Visual Studio already. Adding it to Notepad makes sense.
If I could ask anyone reading this for anything, it would be to open your mind, think before you react negatively and in a knee-jerk fashion, and learn to tell the difference between malicious enshittification and useful new functionality, even if it’s in an app you would like to see remain frozen in time forever. And have some empathy for people who have different needs than you: If these things don’t get in your way, and they don’t, but they do help others, that’s a good thing.
As noted, I use Notepad every single day, all day long, as I do with Paint. And in both cases, the improvements Microsoft has made are positive and useful enhancements. The worst case scenario, literally, is that you may disagree on some individual feature or in general, but you can disable those changes or easily ignore them. That’s not enshittification. It’s the way products and services should be updated.
Granted, I do have a problem with Notepad, of course. It’s advancing so rapidly and in such profound ways that I can’t even keep up with it anymore. Where .NETpad was briefly a superset of Notepad for the most part, it’s now lagging badly, and I’m struggling to implement some version of all those new features. I’m always behind.
But I don’t begrudge Microsoft this advantage. The world’s most valuable company should be able to out-develop a non-developer individual like me. That’s the way things are supposed to work.
I love Notepad. I can’t wait to try the Markdown support. And I respect that you may not like it, while reminding you that you can simply disable or ignore this new feature. All is right in the world, at least when it comes to Notepad.
With technology shaping our everyday lives, how could we not dig deeper?
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