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Can RD Gateway allow SSL certs if the backend RDP computer has a different domain name?

Posted on 2013-01-25
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Last Modified: 2013-02-07
Here is my issue. Our internal AD domain name is not the same as what we own in the outside world.

Lets say our internal AD is called internal.com and the one we own is called external.com

Naturally our internal computers are named desktop1.internal.com, desktop2.internal.com, etc.

our outside services are called webmail.external.com, client.external.com, etc.

for our outside services we just add the SSL to the IIS (or apache) site and we are good, even though internally it might be named e2k10.internal.com.

the problem i am coming across is this:
we've pointed login.external.com to an internal RDP server using port 3389 (NAT). when connecting to it via RDC program we get a cert error saying pretty much "you tried to get to login.external.com but the computer that responded was rdpserver1.internal.com. do you want to continue?"

we have to say yes and then we get access. We would like to secure this so that we dont get the error and use a valid SSL Cert and I'm not sure of the best way. I can't buy internal.com because someone else owns it in the outside world.

instead of making a direct connection to the internal RDP Server,  we were thinking of putting the RD Gateway on a DMZ and see if this would act as a passthrough. But I'm not sure if it will do what we need. We can't change our internal AD domain name and i cant buy the internal.com domain name.

I saw this:http://blogs.msdn.com/b/rds/archive/2009/07/31/rd-gateway-deployment-in-a-perimeter-network-firewall-rules.aspx but it looks like it needs a lot of servers and firewalls in the DMZ and im not sure if i want an AD DC in a DMZ.

Is it possible to put the RD Gateway on a DMZ (or NAT), when the user puts in login.external.com in the RDP program, it will hit the RD Gateway and then send it to an internal RDP server that doesnt have any type of SSL cert?
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Question by:msidnam
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ahoffmann earned 350 total points
ID: 38821746
your RD Gateway needs to be a proxy which terminates the external SSL connection and opens a new won to your internal AD
this means that you need a valid cert for external.com on your gateway
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by:Netflo
ID: 38833332
In answer to your question and supporting Ahoffmanns response.

Yes, you can create a RDG server and put it in your internal or DMZ zone. You would have a SSL cert for login.external.com linked to this server. The RDG would be aware of this certificate and along with respective RAP and CAP policies will allow login to internal assets. Only port 443 TCP needs to be opened up to this server.

If the server is in the DMZ, you need to open up 3389 to your internal network, along with respective ports for domain communication.

The target machines on the inside need to have RD enabled for users to logon. When users logon remotely to a 2008+ server, they will receive a certificate prompt as you don't have the option of buying the internal domain, however you can just tick the box 'don't remind me again' and connect as normal. If connecting to a 2003 box, just connect and no prompt.

Best of luck and get in touch if you have any further questions.
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by:msidnam
ID: 38836944
The main problem we are trying to avoid is having them click the cert prompt. we also ntoiced even if we select dont prompt me again, it still does it.
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Assisted Solution

by:Netflo
Netflo earned 150 total points
ID: 38837141
The don't prompt again should go away, assuming the following option is set on your RDC properties:

Right click RDC icon -> Advanced Tab -> Server Authentication: Connect and don't warn me.
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