Hey Kurtis,I was in the middle of replying and then something clicked for me. I spent the day today working on this one more time and ended up getting it working. I believe my fundamental understanding of a proxy was simply incorrect.
Your comment about the URI prefix was what made it click for me.
Basically all my requests on the client front end were formatted like so "/command". I mistakenly thought that the client would run these with respect to the host it came from (Jetty returns the client as a result of the initial proxied GET to localhost:2000). Apparently, the client ends up realizing it is no longer on localhost:2000 but is now instead on localhost:80 and was calling the requests as such. This would also make sense why "/command" would result in the GET/POST URL as "localhost:80/command".
After your comment, I realized that requests also need to have the URI with respect to the original host rather than the proxy on localhost:2000. As such I changed every instance of "/command" to "./command" and now everything works perfectly.
I did in fact enable the high levels of debug output and could make no sense of them unfortunately...somehow one request ended up in 200 lines of garble (I cleared the log beforehand).