I have a raspberry box running an OpenVPN server that I'm using as a way to connect to use my Pihole installation when outside my home network. This is working without issues.

                     |          HOME NETWORK/Pihole  |
(Remote client)     --   (Open VPN Server )        ---         Internet

Separately I have a remote VPN service that I can connect to via an OpenVPN client from the Pi device. That I tested successfully as well.

                    |          HOME NETWORK/Pihole  |
                           (Open VPN Client )       -            VPN provider

I would like to be combine both services such that the final installation would look like this

                 |          HOME NETWORK /Pihole           |
(Remote client) -- (Open VPN Server) -- (Open VPN Client) --- Remote VPN service

I have tried solutions like the one described in this similar question (Wireguard server with active OpenVPN client) with negative similar results: Once you activate the Open VPN client (tun1) the server (tun0) becomes unreachable.

Here's what the routing table looks like when both interfaces tun[01] are up via dev tun1
default via dev wlan0 src metric 303 dev tun0 proto kernel scope link src via dev tun1 dev tun1 proto kernel scope link src via dev tun1 dev wlan0 proto kernel scope link src metric 303 via dev wlan0

Here's the current output of my openvpn server when I try to connect.

pi@raspberrypi:/etc/openvpn $ sudo more openvpn-status.log
Updated,Sat Jun 29 23:30:41 2019
Common Name,Real Address,Bytes Received,Bytes Sent,Connected Since
UNDEF,x.x.x.x:39159,860,442,Sat Jun 29 23:30:02 2019

This is what the error log looks like

Sat Jun 29 23:34:47 2019 x.x.x.x:28162 TLS Error: incoming packet authentication failed from [AF_INET]
Sat Jun 29 23:34:48 2019 x.x.x.x:28162 Authenticate/Decrypt packet error: bad packet ID (may be a replay): [ #1 / time = (1561869285) Sat Jun 29 23:34:45 2019 ] -- see the man page entry for --no-replay and --replay-window for more
info or silence this warning with --mute-replay-warnings
Sat Jun 29 23:34:48 2019 x.x.x.x:28162 TLS Error: incoming packet authentication failed from [AF_INET]x.x.x.x:28162

Apparently the client connection is getting corrupted?

I also tried the solution in OpenVPN Client and Server on same machine - Server doesn't allow connections when client is connected which I discovered after posting this question, to no avail. This would appear to be directly related to my issue but it's still not working.

  • 1
    I noticed while editing your post that you had a fragment: "Here's what the server log looks like", but I saw no further information. I removed the fragment, but consider this comment a friendly reminder to upload it, if it's different from the existing log information you have. – Jeff Schaller Jul 7 at 14:37

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