I then remembered that I had multiple ports on the machine (it's in the attic, I rarely ever see it) and that awhile ago I had activated a second port (if you don't have multiple NICs, it still is the same issue at the network level) and I checked my routes. Bingo. Switched to the other port and instant connection.
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[07:32] <Rabbi_Bob> I'll puke this out so it's in a log somewhere, it may help someone else
[07:33] <Rabbi_Bob> I'm running Ubuntu 12.04LTS on a headless machine (no desktop\gui\etc) and the box has multiple NICs (5).
[07:34] <Rabbi_Bob> If my client machine (172.25.4.100) connects to the first port of the server the following occurs
[07:34] <Rabbi_Bob> Client -> Server: connection handshake
[07:34] <Rabbi_Bob> Client <- Server: ERROR[ServerThread]: Server: peer_id=2: failed to emerge player
[07:35] <Rabbi_Bob> Client -> Server: continues to send information and server receives
[07:35] <Rabbi_Bob> Client -> Server: keeps going, server knows something is there however cannot communicate back
[07:35] <Rabbi_Bob> Server log: ERROR[ServerThread]: Server: peer_id=2: failed to emerge player
[07:36] <Rabbi_Bob> If I move the connection up to another port, it works
[07:36] <Rabbi_Bob> Server: >route -n
[07:36] <Rabbi_Bob> Destination Gateway Genmask Flags Metric Ref Use Iface
[07:36] <Rabbi_Bob> 0.0.0.0 172.25.4.1 0.0.0.0 UG 100 0 0 eth4
[07:36] <Rabbi_Bob> 172.25.4.0 0.0.0.0 255.255.255.0 U 0 0 0 eth4
[07:36] <Rabbi_Bob> 172.25.4.0 0.0.0.0 255.255.255.0 U 0 0 0 eth1
[07:37] <Rabbi_Bob> eth4 is the working nic
[07:37] <Rabbi_Bob> eth1 is the failed to emerge nic
[07:37] <Rabbi_Bob> and it's the route out causing the issue
For the search engines:
ERROR[ServerThread]: Server: peer_id=2: failed to emerge player
ERROR[ServerThread]: Server: peer_id=3: failed to emerge player
ERROR[ServerThread]: Server: peer_id=6: failed to emerge player