Hi @KarenBDE 

Thanks for posting in our business forum.

KarenBDE wrote

I recently upgraded omada controller to the latest version, then migrated from windows OS to Ubuntu Server. The migration run without problems. I had an OpenVPN running fine but start having problems after the migration. Now, I can access to the VPN if I am inside the same network which isn't the purpose of the VPN, and from outside the network, through internet, it fails to connect due to TLS key negotiation.

Tue Apr  8 11:43:17 2025 TLS Error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)
Tue Apr  8 11:43:17 2025 TLS Error: TLS handshake failed

I've enable ufw on Ubuntu server and allowed in every port that uses omada. Do I need to open the ports for ALLOW OUT?

Any clues?

This does not have anything to do with the controller update or router as far as I can see. Not a problem with the Ubuntu server.

You don't have to set up any port out rules.

Is this a VPN server or the client? Looks like a problem with your network environment.

VPN Connectivity and Access Troubleshooting Guide