
I’m going to say something that would’ve shocked 25-year-old me in a Microsoft polo in the late ’90s:
If this keeps up, I might actually have to switch to macOS.

And if you know me, you know how insane that sounds.
I’m a lifelong Microsoft guy. I love this stuff. I live in SharePoint and SharePoint Online. I’ve built intranets, workflows, project sites, and dashboards on top of Microsoft’s platforms for years. I love the power and flexibility of Windows. I still think classic Outlook (not this “New Outlook” abomination) is one of the best email clients ever created. VS Code? Brilliant. SQL Server? Rock solid. Azure? An incredible platform when marketing buzzwords are not smothering it.
So when I criticize Windows 11 and the direction Microsoft is heading, it’s not coming from some Apple fanboy. I’m the opposite. The only Apple product I really like is the iPhone, and that’s mainly because Microsoft doesn’t make a competitive phone anymore.
I used to work for Microsoft back in the ’90s, when the company still had this almost obsessive focus on making the PC better with every release. Bugs got fixed. Performance improved. New versions felt like upgrades, not traps. You got the sense the engineers actually used their own products and cared when they were clunky.
Fast forward to 2025, and I feel like I’m watching an old friend lose their mind in slow motion.
Let’s start with the obvious: Windows doesn’t feel like “my” machine anymore.
Somewhere along the way, Microsoft stopped treating Windows like a tool I own and started treating it like a storefront I’m allowed to visit. Ads baked into the Start menu. Suggestions in the file explorer. Pop-ups nagging me about OneDrive, about accounts, about subscriptions. I paid for this operating system already, why does it feel like Times Square?
Then there’s the forced cloud and account nonsense.
I’m not opposed to the cloud. I use Azure, I use 365, I use OneDrive. But I want to choose when and how. When Windows 11 starts requiring a Microsoft account just to set up a machine, and keeps closing off the workarounds for local accounts, that’s not “modernization.” That’s a power grab.
Pair that with the TPM 2.0 requirement. Perfectly capable computers suddenly declared “too old” to run Windows 11, not because the processor can’t handle it, but because some security model says you need this specific chip and this specific tie-in to your Microsoft identity. I understand the security argument. I work in environments where security matters. But when security becomes an excuse to lock people into a tracking system, you can understand why folks start side-eyeing the whole operation.
And then we get to the AI invasion.
Look, I’m not anti-AI. I use AI tools. I’m literally typing this to an AI assistant. AI can be incredibly useful. But what Microsoft is doing now with Windows feels less like “augmenting the user” and more like bolting AI onto everything, whether it helps or not.
Copilot in the taskbar, Copilot in Office, Copilot in Windows, Copilot staring at your screen like an over-caffeinated intern who can’t actually do the work you give them. Some of the features are genuinely helpful. But a lot of it feels half-baked, clumsy, or just plain unnecessary. There’s a big difference between “smart assistance” and AI slop added just to look good in a keynote.
And don’t even get me started on Recall the feature that wants to screenshot your entire life on your PC so you can search it later. That one crossed a line. In a world of ransomware, data breaches, sophisticated phishing, and state-level actors, running a permanent camera on my digital life is not a feature to me. It’s a liability. Yes, Microsoft pulled it back and reworked it after the backlash, but it should never have shipped in that form to begin with.
Meanwhile, the basics are breaking.
Updates that take forever and restart at the worst possible times. Performance regressions. Inconsistent UI design. Little bugs that linger across patch after patch. And speaking of bugs the New Outlook absolutely stinks. They took a powerful, battle-tested piece of software and replaced it with a slower, less capable, more webified version that doesn’t measure up for power users. For people who live in email and calendars all day, that’s not a minor annoyance. That’s productivity going backwards.
Here’s the thing that really hurts: Microsoft knows how to do this right.
They’ve done it before. Windows 7 was beloved for a reason. Even Windows 10, for all its quirks, felt like a solid, modern OS that could get out of your way and let you work. The classic, non-subscription Office suite was one of the best productivity toolsets ever built. VS Code is a masterclass in how to win over developers by prioritizing speed and usability.
The problem isn’t that Microsoft can’t make great software anymore. The problem is that the incentives have changed. The revenue is in the cloud, in subscriptions, in telemetry, in “engagement,” in AI demos for investors. Is the home or small-business user running Windows as a local, private, productive environment? That’s not where the big money is. So the OS shifts from serving you to serving the business model.
But here’s the hopeful part and yes, I’m still enough of a Microsoft loyalist to end on a hopeful note:
This is fixable.
Microsoft doesn’t need a spiritual awakening. They need to remember what made them dominant in the first place: build the best tools on earth and let people get work done.
Dial back the ads.
Stop forcing accounts where they’re not truly needed.
Give users back their choice of local vs. cloud.
Treat privacy as a feature, not an obstacle.
Ship AI where it’s actually reliable and helpful after the core experience is fast, stable, and clean.
And for the love of all that is holy in Redmond: fix the bugs before you chase the next buzzword.
I say all this as someone who still wants Microsoft to win. I don’t want to buy a MacBook. I don’t want to move my entire workflow to macOS or Linux. I want Windows to be what it used to be: the best, most flexible, most powerful environment for actually getting things done.
Microsoft can get back there. Someone at Microsoft HQ inRedmond, Washington, please make MicroSoft Great Again (MSGA)
But they’re going to have to decide whether Windows is a product for people or a pipeline for profit. Because if they keep choosing the latter, even die-hard Windows guys like me will eventually walk.
Endnotes
- Windows AI Integration Announcement
Microsoft formally announced its shift toward an “agentic operating system” during its May 2024 Build Conference, emphasizing Copilot as a core UI element and positioning Windows as a canvas for AI-driven workflows.
Source: Microsoft Build 2024 Keynote. - User Backlash to AI-Centric Windows Direction
Pavan Davaluri’s tweet promoting Windows as an AI-first OS received overwhelming negative responses, with users widely criticizing forced AI integration and concerns over privacy, performance, and autonomy.
Source: Public reaction compiled from Davaluri’s official Twitter/X post, June 2024. - Forced Microsoft Account Requirements
Windows 11 setup requires an online Microsoft account for Home and Pro editions, and Microsoft has intentionally removed or patched prior offline account workarounds.
Source: Microsoft Support Documentation, “Windows 11 Installation Requirements,” 2023–2025 updates. - TPM 2.0 Requirement Blocking Older PCs
Microsoft’s mandate for TPM 2.0 rendered millions of still-functional PCs ineligible for Windows 11, despite adequate hardware performance.
Source: Microsoft Windows 11 Compatibility Guidelines, 2021–2025. - Recall Privacy Controversy
Microsoft Recall was pulled and reworked after security researchers demonstrated that Recall’s continuous screenshots were stored in unencrypted databases vulnerable to malware extraction.
Source: Security analyses from CrowdStrike, Ars Technica, and Microsoft’s June 2024 Recall Update Announcement. - Ads and Monetization Inside Windows
Reports confirm Microsoft implemented advertising surfaces in Start Menu recommendations, File Explorer, lock screens, and system notifications despite user backlash.
Source: The Verge, Windows Latest, and BleepingComputer reports, 2022–2025. - Performance and Stability Complaints Linked to Cloud Sync
Microsoft acknowledged in internal notes and developer communications that OneDrive background sync could degrade performance on some Windows 11 systems, contributing to slower UI responsiveness.
Source: Microsoft Developer Blog, “Performance Issues Related to OneDrive Sync,” 2023.
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