Microsoft Breaks Remote Desktop (Again): What SMBs and IT Pros Need to Know

30 Mar

Ah, Microsoft. The gift that keeps on giving. This time, it’s Remote Desktop Protocol (RDP) that’s under the knife—again. Yes, that critical tool you use to manage remote servers, access headless machines, or support end users? Broken. Again. And it’s all thanks to recent cumulative and preview updates for Windows 11.

It seems the January 2025 Preview Updates (KB5034848 for 23H2/22H2 and KB5034204 for 21H2) introduced more than just “improvements and fixes.” They also introduced a lovely little feature where Remote Desktop sessions randomly disconnect. Delightful, isn’t it?

So, what’s going on? Why should you care? And what can you do about it if you’re knee-deep in user complaints and event log errors?

Let’s dive in—and yes, there will be sarcasm.

The Symptoms: RDP Disconnects, No Errors, No Clues

You may have noticed Remote Desktop sessions are suddenly dropping like flies. No warnings, no error messages—just silent disconnections. Some sessions might reconnect, others might freeze. You might even see the Event Viewer light up with fun little nuggets like:

• 0x3000064 (ERROR_CTX_LICENSE_NOT_AVAILABLE)

• SessionID errors

• Authentication failures on otherwise healthy networks

Or maybe nothing at all—just the creeping dread of your support queue filling up with “I can’t log in remotely” tickets.

Microsoft has confirmed the problem in their own words:

“Remote Desktop might disconnect when using a smart card or credential provider if using the January 2025 non-security preview update or later.”

Smart cards. Credential providers. Or basically: anything that isn’t vanilla RDP on an unmanaged consumer PC. In other words, if you’re an IT pro in an SMB setting with Group Policy objects, domain trusts, conditional access policies, or credential hardening: you’re on the hit list.

Wait—January 2025 Update?

Yes. We’re not even in April 2025, but Microsoft is already pumping out Preview Updates with names from the future. Because nothing says “reliable patching” like bending the space-time continuum.

So even if you thought “I’ll wait for the stable releases and skip previews,” you might be shocked to learn that cumulative patches are rolling this RDP bug right into the mainstream channel. It’s not limited to canary testers anymore—this is real, in the wild, and affecting production systems today.

Who’s Affected?

Short answer: anyone running Windows 11 23H2, 22H2, or 21H2 who uses RDP in an environment with:

• Smart card authentication

• Custom credential providers

• Conditional Access Policies

• Group Policies enforcing specific login flows

• Third-party MFA solutions

So basically, any organisation doing remote access with even a shred of professionalism.

For small businesses relying on RDP to manage remote branch sites, servers in co-lo, or simply offer flexibility to staff working from home—this issue is a nightmare. And if you’re an MSP or internal IT support team juggling dozens or hundreds of endpoints, congratulations: this bug just added several hours of mystery troubleshooting to your week.

Microsoft’s Advice? Wait For a Fix.

Let’s pause and admire Microsoft’s official advice:

“We are working on a resolution and will provide an update in an upcoming release.”

That’s it. No workaround. No registry hack. No rollback instruction. No hotfix. Just vibes.

And let’s not forget—this isn’t the first time RDP has been mangled by an update. Remember the NLA nightmare from early 2023? Or the TLS cipher suite regression from 2022? It’s a bit like watching a clown repeatedly fall over the same banana peel.

What Can You Actually Do?

Until Microsoft gets their act together and drops a real fix, you’ve got a few imperfect choices:

1. Roll Back the Update

If you’re lucky enough to catch it early, you can uninstall the offending KB patch. Here’s how:

• wusa /uninstall /kb:5034848

• Reboot

• Test RDP again

But be warned: uninstalling a cumulative update might expose you to other vulnerabilities, so you’ll need to weigh the security trade-off. Thanks, Microsoft.

2. Disable Smart Card Redirection / Credential Providers

This is more of a workaround than a fix, but disabling the affected login mechanisms may help. It’s messy, and not always feasible, especially if those policies exist for compliance reasons.

3. Temporarily Use Other Remote Tools

Desperate times call for desperate software. If RDP is too unstable, consider:

• AnyDesk

• RustDesk

• VNC

• MeshCentral

• A VPN paired with direct MMC or PowerShell access

Yes, it’s like bringing a shovel to dig out a server buried in Microsoft’s nonsense, but it works.

4. Ringfence the Issue

If you’ve got an RMM platform, tag and group affected machines. Isolate them from receiving further updates. Push alerts to admins so they don’t waste time investigating “network issues” when it’s really a broken update again.

Bigger Picture: Trust is Eroding

Here’s the frustrating part. Remote Desktop is not some obscure feature. It’s core infrastructure for countless businesses, especially in the SMB space. And yet, every year, Microsoft finds new and innovative ways to break it.

The steady degradation of patch reliability—particularly in feature updates masquerading as security fixes—is undermining trust. More and more IT pros are disabling Windows Updates entirely and managing patching with third-party tools just to avoid this whack-a-mole game.

It shouldn’t be this way.

But here we are.

Our Rant (Because We Can’t Resist)

How is it that Microsoft—a trillion-dollar company—still manages to ship updates that break essential features without meaningful QA testing?

This isn’t bleeding-edge AI stuff. This is Remote. Desktop. Arguably the most boring, stable, mature service in the Windows ecosystem. But every quarter we seem to get another reminder that nobody is steering the ship. Or if they are, they’re doing it while blindfolded and throwing darts at the update schedule.

To Microsoft: We know telemetry is pouring in. We know the feedback hub is glowing red. Maybe read it before pushing updates to production?

To SMBs and IT admins: You’re not imagining things. It is getting worse. If it feels like you need to test every update in a lab before rolling it out to users, that’s because you do.

Final Thoughts: Test, Isolate, Repeat

If you’re managing IT for a business or multiple clients, treat each patch like a potential landmine. Test before deploying. Avoid preview updates entirely unless you’re prepared to do forensic analysis at 2am. Document everything. And consider using policies to delay feature updates by several months while keeping security updates active.

And remember: this isn’t about fearmongering. It’s about realism. Microsoft’s patching process is opaque, rushed, and often harmful to those who rely on Windows for real-world work.

Noel Bradford

Noel Bradford – Head of Technology at Equate Group, Professional Bullshit Detector, and Full-Time IT Cynic

As Head of Technology at Equate Group, my job description is technically “keeping the lights on,” but in reality, it’s more like “stopping people from setting their own house on fire.” With over 40 years in tech, I’ve seen every IT horror story imaginable—most of them self-inflicted by people who think cybersecurity is just installing antivirus and praying to Saint Norton.

I specialise in cybersecurity for UK businesses, which usually means explaining the difference between ‘MFA’ and ‘WTF’ to directors who still write their passwords on Post-it notes. On Tuesdays, I also help further education colleges navigate Cyber Essentials certification, a process so unnecessarily painful it makes root canal surgery look fun.

My natural habitat? Server rooms held together with zip ties and misplaced optimism, where every cable run is a “temporary fix” from 2012. My mortal enemies? Unmanaged switches, backups that only exist in someone’s imagination, and users who think clicking “Enable Macros” is just fine because it makes the spreadsheet work.

I’m blunt, sarcastic, and genuinely allergic to bullshit. If you want gentle hand-holding and reassuring corporate waffle, you’re in the wrong place. If you want someone who’ll fix your IT, tell you exactly why it broke, and throw in some unsolicited life advice, I’m your man.

Technology isn’t hard. People make it hard. And they make me drink.

https://noelbradford.com