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I know this question has been asked a plethora of times before and I have looked over probably 100 different answers and still can't seem to get this to work.

I'm trying to create a very simple site to site openvpn connection. I have the connection setup and working between the two locations however I cannot get the routing setup to communicate between the devices on the different networks.

Site A (Main):

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Site B:

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VPN Tunnel:

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Trace Route fails after first attempt so the it looks like the route isn't working at all.

Any help would be fantastic!

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Check your firewall rules. It's most likely you simply haven't passed the traffic through. The relevant rules can be found under Firewall->Rules and then on the OpenVPN "pseudo"-interface. – Per von Zweigbergk Jul 24 '14 at 10:06
I have an allow all rule on both sides under the OpenVPN tab. – Scott Dawson Jul 24 '14 at 14:27
Well, it should work. So just a few ideas for what you might check: Have you got IPsec set up with the same IPs that might be interfering with OpenVPN? Try deleting the "route" statement from the OpenVPN config and just going with the "remote site" net. Have you assigned the OpenVPN interfaces to pfSense interfaces? If so you need to set your firewall rules there. Also, it might be that something is out of sync with the webui. Rebooting both sides certainly won't work. Failing that, post your config.xml (you can get it via the Backup feature), redacting out any sensitive info including keys. – Per von Zweigbergk Jul 24 '14 at 17:51

On both Site A and Site B For your VPN Tunnel instead of using try

I believe what you are doing should work, and I think this may be a bug in pfSense - I can't get the way you are doing it to work either, however it works from if I use /30...

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Thanks ill give that a try! Its been over a year since ive worked on this project lol. Ill have to re-orient myself. – Scott Dawson Aug 11 '15 at 13:51

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