Squid can't access service on WAN.

  • I frequently travel and use openVPN to tunnel into my home network. At the same time I have squid setup to proxy web trafic for the VPN. I also have a subsonic media service that is port forwarded through the firewall. From the outside if I access the subsonic server using the WAN address it works as expected. When over the VPN if I access the subsonic server by its LAN address it also works (no proxy for local addresses). Its when I try to use the WAN address over the VPN through squid I get a timeout.

    Its not a big deal to use the LAN address when I tunnel in via openVPN, but as an academic exercise I would like to understand why squid can't access the subsonic service using the WAN address?

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