Hmm so I played around with it a little bit and it looks like where ever I start the tmux session it works fine, but on the other machine it will fail. So if I start a new session from a terminal on the machine I ssh into Secure Shell is broken, but on the target machine it works fine. However, if I start a new session from a Secure Shell terminal then it works fine remotely, but fails when I attach to it locally. Sounds like it is some option that is getting picked up when it first stats, but it's not immediately apparent to me what it is. It also doesn't appear to be a server option since I can run two different sessions at the same time, one started locally and one remotely, that exhibit the opposite behaviors.
--Mitchell