On Mon, Mar 19, 2018 at 2:19 PM, R <[email protected]> wrote:

> Nick, thanks for getting back on this.
>
> Just to make it simpler. Lets say I have VPN concentrator in the cloud and
> it has the tunnel to other customers. Now I want to have guacamole
> installed on a server in the cloud and have a client talk to that VPN 
> concentrator
> (which is also in the cloud) and that client (on guacamole server) will
> have a connection to that VPN concentrator  and tell it to establish the
> rdp/ssh session and session pass it over to the user browser
>
> User Browser -->[Guacamole Server-->Client]-->VPN Concentrator
>
>
So, slight clarification in the traffic flow to make sure I understand:

User Browser -> Guacamole Client -> guacd (Guacamole Server) -> VPN Client
-> VPN Concentrator -> RDP/SSH/VNC Host

I gather from your original question that what you're trying to do is
automate the "VPN Client -> VPN Concentrator" portion of this - that is,
when a connection is attempted from guacd to RDP/SSH/VNC, something on the
system is able to automatically "know" that that connection needs to cross
a VPN boundary, and it establishes that VPN tunnel in order to make the
connection happen.  Correct?

My very first question would be: Why can't the VPN tunnel be persistent?
I'm not familiar with CASB, but it seems like you'd want to set up a
persistent connection between the guacd host and the VPN concentrator in
some fashion that enables the gaucd -> RDP/SSH/VNC connections to happen
very quickly.  The top two reasons I would cite for this would be logistics
(ease of making it happen) and how quickly the connection happens.

Logistically, detecting and establishing the VPN tunnel is more an O/S
issue than it is a Guacamole Server issue.  You'd need some way, on the
operating system, to detect that a connection was being attempted to a host
that is known to be on the other side of a VPN, and you'd need a way to
start that connection up, with some set of pre-defined credentials.  All of
this would need to happen at the TCP/IP stack layer, and isn't really the
concern of Guacamole/guacd.  You could probably write something in either
guacd or into a Guacamole Client extension that accomplishes this for you,
but why?  Again, why not just have a persistent VPN tunnel?  I have a
feeling that the answer for your scenario may lie in how CASB actually
functions, but, again, I'm not familiar with it, so taking the simplified
approach above I'd push for a persistent VPN tunnel.

As far as how quickly the connection happens, the process of establishing a
VPN tunnel usually takes several seconds to accomplish, and if you rely on
something detecting this guacd connection and establishing the tunnel,
there's going to be a delay for guacd and for the end user, which raises
the risk of a timeout during the connection.  It isn't that it makes it
impossible, just something else to consider when trying to automate this
process - making sure that timeouts in Guacamole are high enough to handle
this, and that users expectations are properly aligned.

-Nick

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