I posted this on SuperUser but I thought this would be the better audience. (So sorry for crossposting...)

My employer switched from vpn and rdp to using what our admin calls "rdp over https". Since that switch I find myself unable to connect to the "new" rdp server.

I think the progress is as follows:

  • A rdp gateway-server is connected via tls
  • the requested sever (different from the gateway-server) is then connected through the tls connection.

In windows mstsc-settings the server name is the "internal network name" of the machine I wish to connect. And on the last tab (in German it is called "leistung" - could be activity) I go to the "connection from everywhere" settings and set the gateway-server under gateway-server.

Is there any way to use this scenario under linux (apart from a virtual machine running Windows)?
I am interested in

  • free ideas (e.g. is it possible to create a tls tunnel and connect through that using freerdp/rdesktop?)
  • non-free ideas. As long as they work I'll worry about the costs later.

Free ideas would be better :-)

On SuperUser I got the idea to expose an ssh server and tunnel rdp through it. This is a valid idea but not feasible in my case. I really need a Idea to connect to the rdp server via the gateway-server.



I did some more research and it looks like it's NOT simply rdp tunneled over tls. So, stunnel is not going to work for this scenario.

Now, I still don't know exactly how the gateway works - the protocols could be standard, or they could be some proprietary thing that Microsoft put together. But who knows - you might get lucky and it be something standard.

The next thing I would try is ProxyTunnel. If the gateway is a standard CONNECT proxy, then it might work. The command would be something along these lines -

proxytunnel -a local_port -p gateway_server:port -d destination_server:port

then rdp to localhost on local_port.

I can't promise it'll work, but it's worth a try...

If it's just a simple tls proxy, (plain rdp is tunneled over tls) you can try stunnel.

Set up an stunnel from localhost:some_port to gateway:rdp_port, then point your rdp client to localhost:some_port.

But if there's some other protocol involved (other than rdp and tls) then you're likely to need a client that supports that protocol. In which case, does the MS RDP client work under WINE?

  • regarding stunnel: I would need a setup like this: localhost:1025 via gateway:443 to target:rdp_port. Would that be possible using stunnel?
    – Nils
    Oct 12 '10 at 20:07
  • regarding mstsc/wine: no (tried it), see also appdb.winehq.org/objectManager.php?sClass=version&iId=17714
    – Nils
    Oct 12 '10 at 20:38
  • regarding proxytunnel: It does not work. However I did not manage to get error-messages out of proxytunnel, so I do not know what the problem was..
    – Nils
    Oct 17 '10 at 20:09
  • Without a server to test against, or more information about the protocols in use, I'm afraid I don't have any other suggestions.
    – Bill B
    Oct 21 '10 at 1:22

There is one (!) software that can do this:
http://itap-mobile.com/desktop/rdp/ brings iTap - an rdp connection software that comes for 20 € plus tax. It is not open source but it is a solution to my "problem"... They have a test-version, too.

iTap seems to run under GNU/Linux and Mac.
I have tried it with my employers setup and it works flawlessly.

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