VPN, RDP, and RRAS connections issues after Windows Server updates

If you really think about it, it is a bit funny to see how we receive all of these fix updates which inevitably end up breaking even more stuff.

No, Windows 10 and 11 aren’t the only Microsoft-designed software to take hits after every rollout, as Windows Servers aren’t immune to these blunders.

That being said, note that this month’s Windows Server updates are causing quite a few issues, including VPN and RDP connectivity problems on servers with Routing and Remote Access Service (RRAS) enabled.

Yes, we are talking about last week’s Patch Tuesday release, which includes:

• Windows Server 2019 2012 R2 KB5014746
• Windows Server 2019 KB5014692
• Windows Server 20H2 KB5014699
• Windows Server 2022 KB5014678 

Latest Windows Server updates cause major issues

UPDATE: It took a little while, but Microsoft has finally confirmed Internet connectivity issues affecting servers with Routing and Remote Access Service (RRAS) enabled after installing Windows updates released as part of this month’s Patch Tuesday.

Furthermore, Redmond officials say that client devices might also experience problems after connecting to the affected servers, with the servers also likely losing their Internet connection in the process.

The company has now revealed that these issues have been addressed in last week’s optional Windows cumulative update previews.

That being said, users that are on newer Windows 10 releases, Windows 8.1, Windows 7 SP1, and several Windows Server versions also affected by this issue will likely have to wait for a fix until next month’s Patch Tuesday rollout.

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After installing the above-mentioned updates, Windows admins started to report experiencing multiple issues that could only be resolved after completely uninstalling the updates.

The one that stands out the most is the servers freezing for several minutes after a client connects to the RRAS server with SSTP.

In case you weren’t aware, RRAS is a Windows service that offers additional TCP connectivity and routing features, including remote access or site-to-site connectivity with the help of virtual private network (VPN) or dial-up connections.

Same here. I had to roll back updates on two RRAS servers. Disabling NAT was not an option as this is what the servers are supposed to do.

However, even though the Internet is buzzing with complaints in regards to this matter, Microsoft hasn’t yet acknowledged these connectivity problems, which means we don’t have an official fix right now.

That being said, the only way to address these issues on affected servers is to uninstall the corresponding cumulative update for your Windows Server version.

How can I fix these problems?

As we mentioned above, there are no fixes yet, and the only thing you can do is to actually uninstall these cumulative updates.

However, we have to warn you that, since Microsoft packages all security fixes within a single update, removing this cumulative update may fix the bugs but will also remove all security patches for vulnerabilities addressed.

So, seeing how there’s no winner winner, chicken dinner situation here, be sure that restoring RDP or VPN connectivity on your servers is worth the increased security risks you are taking when uninstalling the updates.

If you are an admin, use one of the following commands to uninstall:

Windows Server 2012 R2: wusa /uninstall /kb:KB5014746
Windows Server 2019: wusa /uninstall /kb:KB5014692
Windows Server 20H2: wusa /uninstall /kb:KB5014699
Windows Server 2022: wusa /uninstall /kb:KB5014678

Are you also experiencing these problems on your Windows Server machine? Share your experience with us in the comments section below.