After some trial and error, it ended up being a code error, that would
cause a stack overflow if the connection string wasn't set correctly, which
wasn't for the cloud.
I would expect to see a more meaningful error while in the cloud since I
enabled all the logging features.
Not sure how this works but apparently the server itself was timing out
and the other server, the gateway I believe, didn't have a clue on what was
up. Just my assumption.