http://sshkeybox.com/img/keybox_dia.jpg
Not only does it create a single point of failure in the Administration, but the third case illustrates that this is some kind of feature, advertising blocking normal SSH traffic to the server network, instead replacing it with HTTPS traffic.
Please don't do this. Just accept SSH and learn to deal with it. If you can't, maybe systems administration is not for you and you should pay someone to do it.
The reality is this is stupid and just leads to people working around the problem. Take for example corkscrew, which allows you to tunnel SSH over HTTPS proxies, without losing any of it's port forwarding or other juicy features.
If you feel like you really need to embarass them you can ofcourse run something like sshuttle over the top providing automatic VPN routing over this rogue SSH tunnel.
Worse yet they might install KeyBox on their AWS deployment because they don't have SSH outbound, which then promptly gets pwned because it's a relatively unproven Java web application rather than a battle-hardened unix staple (i.e sshd).
Corp networks and infosec departments are a joke.
In terms of auditing all you need to do is make proper use of *nix permission model and then enable sudo input/output logging and control access to sudo via LDAP groups. Send all of your sudo logs to centralized logging system like Splunk/ELK/fluentd/Flume etc.
I regularly defeat most policies if I really have to get work done but the real deterrent, sadly, is for employees to be fearful of getting caught and having to deal with the immense mountain of bullshit paperwork and training that is likely to follow. Completely meaningless paperwork filling is a form of disciplinary action in my opinion.
* Use of SSH is discouraged, because the traffic is encrypted, and the Air Force wants to be able to read all the traffic in and out of boxes.
* If you do get a waiver for SSH, the system admins require you to hand over all your SSH private keys, so that they can decrypt the traffic, read it, and re-encrypt it.
Building a single point of compromise has no advantages over this and many disadvantages beyond just security.
Think if you had a DB with financials (credit cards and such) in a isolated DMZ with SSH inbound/outbound blocked
How can you dump the DB and copy it off if all the traffic was "proxied" through this?? It's not like you can scp a tarball anywhere.
You can't forward ports and expose the DB outside of the DMZ either.
And it doesn't take admins to setup auditing or disable forwarding, you have physically disabled it.
I got to say I don't understand the single point of compromise thing. A single point of failure is a bad, but the less points of compromise the better. You identify your critical systems, you protect your critical systems. Spreading things out doesn't make you more secure.
Here is an old white paper on some things to think about SSH in your infrastructure.
http://www.sans.org/reading-room/whitepapers/vpns/security-i...
Your right in saying this is an unproven application!