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  • This basically a situation where I need to map a plurality of addresses.... all targeting a single port (1433) to a single address (localhost) targetting multiple ports (unique jump host connections for a particular server).
    – Triynko
    Commented Feb 25, 2020 at 19:58
  • Is it possible to use other means of connecting to the jumphost than SSH? Specifically, with a VPN server this would be a simple route, or at worst iptables DNAT on the jumphost.
    – grawity_u1686
    Commented Feb 25, 2020 at 20:01
  • I figured it out. I'll write up an answer. I just used a combination of the HOSTS file and netsh interface portproxy to add the port redirects. The TRICK is that the "listenaddress" cannot be remote. It has to be local. It doesn't have to be "localhost" (127.0.0.1), but it does have to be a local address LIKE 127.0.0.0/8. So basically, use HOSTS file to force remoteAddressA onto an unused "local" address like 127.123.0.0, and then add a portproxy redirect for port 1433 on locl address 127.123.0.0 to port 5001 on localhost 127.0.0.1. That routes it through the tunnel.
    – Triynko
    Commented Feb 25, 2020 at 20:46