It seems the web filter was just dropping the packets for this "non-standard" port.
I found two ways around this issue, 1 on my own, and the other with the help of a Barracuda tech. Both have their advantages and disadvantages.
1. Add it to IP block/exempt with that specific port, the disadvantage is that it bypasses the filters.
2. Add the port to the HTTPS ports, the disadvantage here is that it opens up that port, however you can lock this down to a specific IP address on your firewall if you want the extra security.
Thanks for your response guys. It prompted me to change the verbage I was using when doing web searches for this issue.Go to the full post