[stunnel-users] Using stunnel to RDP into a SSL-enabled Windows box

Daren Krive daren.krive at gmail.com
Tue May 11 04:39:34 CEST 2010

Hi everyone,

First of all I apologize if this has been asked before or if I am totally
misunderstanding the purpose of stunnel altogether.  If so please bear with
my ignorance.

I am an IT consultant and I manage about 20+ Windows-based servers.  Some of
these servers are accessible via VPN while others are accessible directly
via RDP over the Internet.  For those that are exposed to the net I am using
the SSL certificate feature of Remote Desktop by going into “Terminal
Services Configuration” and configuring the connection to use an SSL (most
of the time a self-signed cert).

I can connect to these machines no problem from Windows and I get a “lock”
icon in my RDP client.  However I cannot connect to these machines using
rdestkop under Ubuntu.  I have determined that if I turn off the requirement
to use SSL on the server side (and instead allow the connection to use the
built-in encryption of RDP) then I am able to connect with rdesktop.

I would very much like to avoid rebooting just to connect to these servers.
I am also not willing to remove the requirement for the SSL connection.

Is there a way I can use stunnel on my Ubuntu box to first establish a
secure SSL connection and then use rdesktop over that connection?

I have searched high and low for info on this and found nothing.  I have
found instructions on how to use the Windows version of stunnel to secure
RDP but that isn’t what I am trying to do.  The server is already using an
SSL cert to encrypt the connection (not sure how many people know Windows
2003 and up can do this).  I am looking to get around the apparent lack of
SSL support in rdesktop.

Best regards,
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