Windows Can't Be Trusted Anymore

TL;DR: After a brutal mission prep where Windows fought us at every turn—Hyper-V networking dying randomly, RDP clients lagging inexplicably, Delivery Optimization not delivering, WSL2 refusing to work—I’m calling it: Windows as a server platform is becoming abandonware. Microsoft has moved to Linux themselves. The writing is on the wall. Start your transition plan now. For desktops, macOS is best, but Linux (Pop! OS) is now genuinely better than Windows. It’s insane that this has finally become true.

The Mission From Hell

I just finished a NASA mission prep. We fought Windows for days. Not the interesting problems—the infrastructure problems. The “why doesn’t this basic thing work anymore” problems.

Here’s what we encountered:

1. Hyper-V: From “Never Great” to “Actively Hostile”

Hyper-V was never my favorite virtualization platform, but it worked. Past tense.

The virtual ethernet adapters it creates for its vSwitch concepts? They work for 5-10 minutes. Then they don’t. No error message. No event log entry that makes sense. Just… stops passing traffic. Disable and re-enable the network card – works again. Wait 10 minutes – dead again.

We burned days on this before giving up and finding workarounds.

2. RDP: Twenty Years of Trust, Gone

I’ve been using Windows Remote Desktop clients for 20 years. They were rock solid. Microsoft’s one genuinely great protocol.

Now? Massive input and output lag. Not network lag—the network is fine. The Microsoft macOS RDP client connects to the same machines perfectly. Third-party RDP clients work fine. But the Windows RDP client? Unusable.

This started sometime in the last six months. No configuration change on our end. Just… broken now.

3. Delivery Optimization: The Name Is Aspirational

We needed to upgrade 10 laptops from Windows 10 to Windows 11. Microsoft’s Delivery Optimization is supposed to help here—it’s a peer-to-peer system where machines on the same LAN share downloaded content with each other. Download Windows 11 once, and the other machines grab it from their neighbor instead of re-downloading from Microsoft.

Great in theory. In practice? The 2nd, 3rd, 4th downloads would jump to 5% quickly (grabbing cached data from the first machine), then slow back down to internet speeds for the remaining 95%.

The feature exists. It pretends to work. It doesn’t actually work.

I dug in because there was no way I was going to download 10 * a 7.7GB Windows 11 upgrade file on hotel Wifi. Microsoft hides all details of how Delivery optimization works, but warp.dev and I reverse engineered a good deal. We figured out Microsoft was only storing 450MB of that 7.7GB file. Perhaps I'll write more on that adventure another time.

4. WSL2: I’ve Literally Never Gotten It To Work

Windows Subsystem for Linux 2 should be the killer feature that keeps developers on Windows. Microsoft’s own documentation makes it sound seamless.

I’ve tried on at least five different machines over the past three years. I’ve never gotten WSL2 to work reliably. The networking issues alone have spawned thousands of Stack Overflow threads. Reddit’s WSL2 communities are basically support groups. Microsoft’s own Q&A forums are full of “my WSL2 can’t connect to the internet after an OS update” posts with solutions that involve uninstalling Windows updates.

A feature that breaks every time Windows updates isn’t a feature. It’s a liability.

What Saved Us: Warp.dev

We wouldn’t have gotten out of this mission prep alive without Warp.

I’ll say it again: Warp.dev is the most under-rated, under-hyped product in AI. It took a very difficult mission prep—one where we were drowning in inexplicable Windows failures—and made it survivable.

When something breaks mysteriously, Warp’s AI could help us diagnose, work around, and move forward. Not perfectly—more on that below—but enough to keep us moving.

What’s Going On?

Three things:

1. Windows as a Server Is Becoming Abandonware

Microsoft has essentially let Windows as a server platform turn to dust. This isn’t speculation—Microsoft themselves run Azure on Linux. Their own infrastructure teams moved away from Windows Server years ago.

When the vendor doesn’t use their own product, you shouldn’t either.

The symptoms are everywhere: features that half-work, bugs that never get fixed, documentation that’s out of date, networking stacks that randomly fail. Nobody’s minding the store.

2. Open Source + AI Is A Superpower

Open source always had an edge over closed source for troubleshooting. But open source + AI is something else entirely.

You might not have time to read the source code of every tool or platform you use. But AI can. Something doesn’t work on Linux? Point your AI at the error message, the relevant source files, and you get a real answer—often a fix.

On Windows? AI (including Warp) can help with the symptoms, but it can’t read between lines of source code that it can't see. It can’t really know what’s happening inside the black box. It suggests workarounds instead of fixes, because workarounds are all that’s possible.

3. Windows Is Showing Its Age

Here’s the part that still surprises me: we ended up converting two laptops to Pop!_OS.

We couldn’t get Windows 11 to work correctly on a laptop designed for Windows. An HP EliteBook 840 G6—a mainstream business laptop. Windows 11 installed but was buggy, slow, and unreliable.

Pop!_OS? Just worked. Ethernet, WiFi, graphics, sound, Bluetooth—everything. Docker worked. Desktop apps worked. YubiKey authentication worked. It was faster than Windows 11 on the same hardware.

Linux on the desktop has been “almost ready” for 20 years. I’m now saying what I never thought I’d say: for many use cases, Linux on the desktop is better than Windows.

What To Do Moving Forward

If You’re Running Windows Servers

Start your transition plan now. Whether you’re a tech nerd or business professional, begin moving away from Windows in server roles.

I believe a few good years are left—Windows Server isn’t going to stop working overnight. But the pains and strains are already showing. The trend is clear. Pace yourself, but have a plan.

If You’re On Desktop

macOS is still the best desktop experience if you can afford it and it fits your workflow.

But if you’re choosing between Windows and Linux? Linux is probably better now. Not for gaming (yet), not for every niche application, but for general productivity and development work? Pop!_OS, Ubuntu, or Fedora will give you fewer headaches than Windows 11.

It’s insane that this has finally become true. But here we are.