pfSense

Do you have both of these OpenVPN interfaces assigned as OPT interfaces?

Seeing your full config might be helpful.

Also packet captures from both OpenVPN interfaces when you are seeing this behavior.

I've tried assigning both OpenVPN instances to an OPT interfaces, this does not seem to have any effect.

Which config would you like to see?

Also, getting 500 error from RedMine trying to attach any file... the tcpdumps clearly show round robin behavior.

Uploads to here should be fixed. It would be helpful to see exactly how your outbound NAT rule(s) are configured.

You should try to assign both OpenVPN interfaces as OPT interfaces and make sure your outbound NAT rules are crafted such that the proper rules are set on both interfaces there. So you'd have one rule per assigned OpenVPN interface, and not using the 'openvpn' choice in the interface field.

If that works there may be an issue with that 'openvpn' choice and outbound NAT.

K Mullin wrote:

I have tried individual Outbound NAT rules for each OPT interface, this actually doesn't work even with a single OPT interface and a single openVPN client.

Actually, scratch that. I your suggestion worked. Apparently you need to "enable" the OPT interfaces after "assigning" them to the openvpn client.

Both tunnels are now up, with 0 packet loss through either.

Is there anything else I can provide for testing/debugging while I have this setup?