Connection problems with the new version of Windows

AbrahamNeo

Good morning,

I am raising this issue to see if you can help me figure out what is happening with my VPN. It has stopped working and is throwing the error: "TLS Error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)." This is only happening on Windows 11; I verified that it works without issues on Windows 10 and macOS, so I have ruled out my VPN server or my network as the cause. I hope you can help if you are encountering the same issue.

Regards,

The Johan

That error message basically says that the connection to your server could not be made. If another device on the same network can connect just fine, it is unlikely to be a problem with the server or that network. Then it's most likely some odd problem within a Windows 11 setting itself, like a firewall or antivirus program blocking the connection somehow, or some bad network settings or such.

Mohammad Montazeri

To make the Windows comparison useful, could you add the exact OpenVPN app/version and Windows 11 build, and confirm whether all three devices use the same profile, server hostname, port/transport and local network? A working connection on another OS is a useful control, but the failing Windows machine could still resolve or route to a different endpoint.

Please compare the resolved server address and route on the working and failing machines, and share only the redacted client-log lines immediately before the 60-second timeout. If you administer the server, checking whether that same attempt reaches its log would help distinguish “nothing arrived” from a later handshake failure. Keep the connection settings unchanged for that comparison; a successful TCP port test would not establish that a UDP VPN path works. That evidence should make the firewall/network-setting possibilities already mentioned easier to narrow down.

AI-assisted reply; I work on a VPN service.

AbrahamNeo

Thank you for your comments.

Please note that the VPN was operational. To try to resolve the issue, I performed the following tests:

Testing with different versions of the OpenVPN application (both older and recent).
Certificate validation: they work correctly on macOS and on earlier versions of Windows (such as 25H2). The failure occurs only on Windows version 24H2.
Testing on different networks (home and mobile), yielding the same result.
Configuration adjustments to the connection file, without success.

Given that configuration options have been exhausted and the connection cannot be established, we believe this is an incompatibility issue with Windows 24H2; therefore, this VPN solution is no longer viable.