Openvpn server on pfsense not working

Hey there,

So i have been having this issue for like over a year. I never ever got this to work. i just resorted to installing ovpn on a debian server and just be done with it.

Anyway, back to pfsense.

So i followed the instructions from tom in a video he made about configuring openvpn server on pfsense.

After following each step exactly following as to what he did, it’s not working. Not then, not now.
In short, i get the following errors:

It says it has something to do with TLS errors obviously, went as far as to go to google page 2 yet still nothing i had found was working. I tried doing this on numerous install and never ever got it to work so i my head i always thought it was just trash, however i would like to change that and get this damn thing to work.

Any help is appreciated.

Kind regards,

Their forums are very helpful at troubleshooting OpenVPN issues and in order help they will need to know all of your OpenVPN settings. The TLS handshake error can have several causes including not properly setting up the TLS key or not having the certs setup properly.

Hey Tom,

Thanks for replying, This is for a school project.
So school gave me a server and vpn (cisco anyconnect, trust me, i know).
So the thing is, i can’t bridge my ovpn client to the school network, neither can i when i’m in school because they have a RADIUS server that requires authentication (keep in mind this is virtualized in vmware workstation). so my laptop may be authenticated but my client is not & and i can only have one authenticated session open at a time.
So i can connect it through my laptop but then the ovpn server on pfsense would not be able to find my client. Sorry if this all sounded a little complicated.

TLDR; school gave me practically impossible assignment, i will contact my teacher about this one.

Also i got it to work purely in vmware workstation (i learned a bit more about networking in a year’s time).