Soft ComputersIf your team uses Remote Desktop to connect to a Windows Server, whether from home or between office locations, you may have run into a nasty problem this week. Microsoft confirmed on September 14, 2026, according to BleepingComputer, that its September Patch Tuesday updates are causing Remote Desktop Services (RDS) failures on Windows Server. Connections that worked fine on Friday are now dropping or refusing to start entirely.
This is not a configuration error on your end. It is a broken update from Microsoft. And it is exactly the kind of problem that stops work cold, especially for businesses running hybrid or remote teams.
What Actually Happened
Microsoft releases security and feature updates on the second Tuesday of every month, a cycle the industry calls Patch Tuesday. The September 2026 batch included patches for dozens of known vulnerabilities, which is legitimate and necessary work. The problem is that somewhere in that update, something broke the Remote Desktop Services stack on Windows Server.
RDS is the Microsoft technology that lets users log into a server remotely, see a desktop, run applications, and access files, just as if they were sitting in front of that machine. Many Canadian SMBs rely on it for staff who work from home, for accessing accounting software hosted on a server, or for IT teams managing infrastructure remotely. When RDS breaks, people cannot do their jobs.
Microsoft has acknowledged the issue publicly. A fix is being worked on, but as of the time of writing, no patched update has been released.
Why This Keeps Happening
Broken Windows updates are not a new story. In June 2026 we wrote about a separate update cycle that caused failures on business PCs. These incidents share a common thread: updates are pushed automatically, something breaks in production, and businesses are left scrambling.
For a small business without a dedicated IT team, the reaction is usually one of two extremes. Either updates are applied the moment they drop, which exposes you to problems like this. Or updates get delayed indefinitely out of caution, which leaves known security vulnerabilities open on your servers. Neither extreme is right.
This is the core of what managed IT is supposed to solve. A managed services provider tests updates in a controlled environment before pushing them to your production systems. They watch vendor advisories and hold problematic patches until Microsoft releases a fix. And when something breaks anyway, they have the access and tools to respond immediately rather than leaving you to call a support line.
What You Should Do Right Now
- Do not uninstall the September updates yet. The updates also contained real security patches. Removing them blindly may re-expose your server to vulnerabilities that were just closed. Wait for guidance specific to your environment.
- Check Microsoft's Windows Health Dashboard. Microsoft maintains a known issues page for each version of Windows Server. The September RDS failure is documented there. That page will also show when Microsoft releases a fix.
- Have a workaround ready for your team. If RDS is down and staff cannot connect, you may need a temporary alternative. Tools like Microsoft Teams remote control or a VPN with direct file share access can bridge the gap for a day or two.
- Document who is affected and how. If you work with an IT provider, they need to know which servers are running which version of Windows Server and which user groups depend on RDS. Get that information organized so any fix can be deployed quickly and in the right order.
- Do not rush to apply the next update without testing. When Microsoft releases the fix, it will come through the same Windows Update channel. Confirm with your IT team that the fix has been validated before pushing it broadly.
The Broader Point About Patch Management
Patch management sounds administrative. In practice, it is one of the highest-risk activities in your IT environment. You are regularly installing new code written by a large vendor, across every machine in your business, often overnight and without anyone watching.
Done well, patching closes security holes before attackers can use them. Done carelessly, it takes down the systems your staff depend on every Monday morning.
Our team manages this for clients by keeping a staging layer, monitoring Microsoft's advisory feeds, and using a controlled rollout schedule. Servers that run critical services like RDS get updates applied after we have confirmed the patch is stable, not before. That delay is usually 48 to 72 hours, which is enough time for problems like this to surface in the community and for us to hold the patch.
If your business is applying updates manually or relying on default automatic update settings, you do not have that buffer. You are running the same risk this week as every other unmanaged server out there.
What We Recommend
If your staff are locked out of Remote Desktop right now, call your IT provider today. This is a known issue with a known cause and there are workarounds available while you wait for Microsoft's fix.
If you are managing your own Windows Server environment without professional support, this is a reasonable moment to reconsider that approach. The cost of a managed services arrangement is predictable. The cost of a day of lost productivity across your team, plus emergency support calls, is not.
We are available to assess your current patch management setup and put a proper schedule in place. Reach out to our team and we will take a look.