Has anyone experienced intermittent Remote Desktop connection failures after installing the September security updates on Windows Server 2019? The connection sometimes works, but after disconnecting, reconnecting gets stuck at "Securing network connection" and eventually fails. What is the recommended remediation?
4 Answers
The reported symptom is not just a timeout: connections may work intermittently, then fail after disconnecting and remain stuck at “Securing network connection.” That behavior is consistent with the RDP issue addressed by the out-of-band updates.
The issue can be severe enough to make a terminal server inaccessible. In one case, RDP stopped working entirely and the server had to be reset, so applying the out-of-band update promptly is recommended.
The September 14 out-of-band patch is the main fix to try. Download the appropriate update from the Microsoft Update Catalog, install it on the affected server, and restart it before testing RDP again.
Yes, this was a known issue with the September updates. Microsoft released an out-of-band update intended to address the RDP failures. Install the package that matches your Windows or Server version; for the affected releases, the listed KBs include KB5129195, KB5129236, KB5129238, and KB5129239.

Thanks. I may also be seeing problems with locally hosted, non-FCI SQL services, so I’ll check whether those are related to the same update.