OpenVPN on Windows having handshake error

  • Good Morning All,

    So I have started at a new company as the only IT guy. This is also my first experience in using PFSense and I am having some issues that I am hoping someone could help me out with.

    So on the PFSense box, through the GUI, I have created the User account by going System –> User Manager --> Users and clicking Add in the bottom right corner. I put in the username and password, the full name and leave the expiration as is. I create the user certificate as well and then click save. I then export the config, install it on the laptop and the user can connect.

    Now yesterday I restarted the firewall and this morning he can't connect, gets a TLS handshake error. But everyone else who has been setup can connect. Am I missing something here? This can be fixed by downloading the installer again, reinstalling it and he connects but if I use the installer from the previous install it does not connect.

    The version of PFSense is 2.3.3 and I will be updating it later on today to the latest release, hopefully that might fix the issue? OpenVPN according to package manager is up to date as well.

    Thank you for the help. :)