Some connection issues when running vpn (to my company)

Hi, first post. To start off, love home assistant. I literally dumped windows on my machine so I could benefit from the full experience.

So I run home assistant supervisor on my main home machine on unbuntu (I know not supported, so fair to say take a hike here), but I also need to use cisco anyconnect to connect to my office computer for remote working. I’ve found that some connections fail when I have anyconnect running and am guessing it is due to a configuration, route, or perhaps a dns. I’m just not that knowledgeable in these areas.

Some of the errors I have seen (occur when i restart the server with vpn running):
Cannot connect to host api.github.com:443 ssl:default [Try again]

telegram.error.NetworkError: urllib3 HTTPError HTTPSConnectionPool(host='api.telegram.org', port=443): Max retries exceeded with url: /bot1984577737:AAHMpgVnW5MXibix-0tWrWi9VD-GkFmu3Fs/getMe (Caused by NewConnectionError('<telegram.vendor.ptb_urllib3.urllib3.connection.VerifiedHTTPSConnection object at 0x7f62aa2640d0>: Failed to establish a new connection: [Errno -3] Try again'))

I have:

  • confirmed my vpn is running split tunnel
  • done a bunch of traceroutes from the console to the servers above and they resolve the ip and don’t show any ip’s that belong to my corporate network
  • confirmed the ha dns servers contain my host machine ip and 1.1.1.1

I’ve noticed both the above errors are port 443/ssl, so am wondering if that is related? I’ve also got nginx setup + duckdns for remote access, so perhaps that could be related?

Sorry for the barfing of details–any suggestions for how to further troubleshoot would be immensely appreciated.

Just want to update I found a solution to this–i just installed OpenConnect and I am able to connect to my work vpn and it DOES NOT appear to mess with my iptables like anyconnect does. It is possible that less things are routing to my work vpn, but I really only need to be able to open up rdp connections and those work, so I’m good to go.