Tag Archives: watchguard

Debian Linux openvpn connect to Watchguard VPN

I have a Debian Server that I wanted to connect to a Watchguard VPN.

OpenVPN is the tool that I used and the following is based on JoKi’s excellent blog entry with my own adjustments to address the issues that I found.

To start you do need to install and run a connection using the Watchguard MobileVPN on your Windows box to get the configuration files in

C:Usersyour_user_name_hereAppDataRoamingWatchGuardMobile VPN

It took me a while to work out that I had to run it to get the config files created, installing alone is not enough.

Installation in Debian is straightforward

#apt-get install openvpn

Once that is done go to the newly created /etc/openvpn and copy the files from the abovementioned Watchguard directory to it.


Now it should all be good to go.

#openvpn --config client.ovpn

Except that I was getting all sorts of errors and warnings……

Wed Nov 12 12:16:50 2014 VERIFY X509NAME ERROR: /O=watchguard_technologies/0.0=f ireware/CN=fireware_sslvpn_server, must be /O=watchguard_technologies/ITU-T=fire ware/CN=fireware_sslvpn_server
Wed Nov 12 12:16:50 2014 TLS_ERROR: BIO read tls_read_plaintext error: error:140 90086:SSL routines:SSL3_GET_SERVER_CERTIFICATE:certificate verify failed
Wed Nov 12 12:16:50 2014 TLS Error: TLS object -> incoming plaintext read error
Wed Nov 12 12:16:50 2014 TLS Error: TLS handshake failed
Wed Nov 12 12:16:50 2014 Fatal TLS error (check_tls_errors_co), restarting
Wed Nov 12 12:16:50 2014 SIGUSR1[soft,tls-error] received, process restarting
Wed Nov 12 12:16:50 2014 Restart pause, 5 second(s)

Everything I read said that the certificate files would be the issue, but that was not logical to me as they were direct from the Watchguard device and not ones I was creating.

But I checked them anyway with

#openssl verify -CAfile ca.crt client.crt

Next I tried addressing the verify X509 Name error by changing the client.ovpn file entry changing




and messed around with that for a while until in disgust I commented the line out to try and confirm that it was triggering the error.

Of course, it worked first time !!!  Argghhhh!!

So the answer to the above is to remove the tls-remote line completely from the configuration file.

tls-remote “/O=watchguard_technologies/ITU-T=fireware/CN=fireware_sslvpn_server”

Either comment it with # at the start of the line or delete it.

Once that was sorted I had a working connection all that remained was to

#mv client.ovpn client.conf

create an auth.txt file with


#chmod to 0600 auth.txt

Edit the client.conf file to have

auth-user-pass auth.txt

and finally start it as a service
#service openvpn start client

and the last bit of the puzzle, to add it as a service to automatically start

#update-rc.d openvpn enable

Thanks to JoKi for getting me started.