OpenVPN S2S Routing Between My LAN and my DO Private Lan

Hey everyone, not sure where to post this… I posted this in /r/pfsense as well but figured i’d try here as well.

I’m trying to do a site-to-site vpn using openvpn and running into some routing issues.

On Premise LAN

VPN Tunnel Network:
My PC:

Remote LAN

VPN "Client":
Ubuntu Testbox:

I’m using ubuntu 14.04 w/ openvpn_as deb 0.2.10 installed on it on a digitalocean droplet.

I’ve got the vpn connected site to site. I can ping both ways from My PC <-> VPN Client using the VPN clients LAN IP (and not the tunnel net ip) and my IP.

Where i get the hiccup is, trying to contact any other machines on my remote lan from my on-premise lan, i can’t talk to them or from them.

For example, from “ubuntu testbox” I can ping fine. I can’t ping From my machine I cant ping

Here is my config file that was dumped from pfsense, and here is a screenshot of my openvpn server configs.

I moved some things around, specifically I commented out pull as openvpn was throwing errors about it and tls-client when trying to connect.

That error was Options error: Parameter --pull can only be specified in TLS-mode, i.e. where --tls-server or --tls-client is also specified. Use --help for more information.

Submit an answer

This textbox defaults to using Markdown to format your answer.

You can type !ref in this text area to quickly search our full set of tutorials, documentation & marketplace offerings and insert the link!

Sign In or Sign Up to Answer

These answers are provided by our Community. If you find them useful, show some love by clicking the heart. If you run into issues leave a comment, or add your own answer to help others.

Want to learn more? Join the DigitalOcean Community!

Join our DigitalOcean community of over a million developers for free! Get help and share knowledge in Q&A, subscribe to topics of interest, and get courses and tools that will help you grow as a developer and scale your project or business.

after a bit more testing, i think this is related to packet filtering. I’ve read a few other posts with similar scenario’s where DO drops mismatch IP packets. for source/dest.