I cannot login to Octopus once a VPN connection is made to production environment

Here’s my setup. Octopus server on a Windows Server 2012 R2 machine is located on the local network (no VPN needed). Dev and test are located on the same network and I have no issues deploying to these servers. Staging and production are in an offsite hosting facility that require a VPN connection. Once I start the VPN connection on the deployment server I’m no longer able to log into Octopus because it cant locate my active directory account anymore. I’ve tried adding the AD server name to the hosts file but that didnt seem to help.

The strangest thing is if I’m already logged into Octopus before the VPN connection is established I’m still able to use octopus server and Octopus sees staging and production tentacles with a health check. One of the problems here is the session times out after a short period of time. Also, when deploying an application the variables in the process steps are not replaced correctly and show up as ‘#CustomVariable’. I can only assume the reason for this is because the SQL server DB also uses AD and cannot connect.

Any help with this is much appreciated.

Hi Christopher,

Thanks for getting in touch. My guess is that once the VPN connection is established, DNS requests are being routed over the VPN. Most VPNs have an option like “Use as default gateway” which you may need to try and disable.

A good test would be to remove Octopus from the equation, and just remote desktop to the Octopus server, and see what happens when you establish the VPN. Can you still open SQL Server Management Studio to connect to the database, can you browse to other computers on your local/dev network, etc.


Thanks Paul but I was finally able to figure out the issue.

I needed to run nslookup to find the ip and hostname and then add that to the server hosts file. After this everything started working.