Connecting to Terminal Servers using RDP RD Gateway Settings

RDP LogonTerminal Server/Role ServiceRDP RD Gateway Server
I have two Terminal Servers with Windows 2008 R2 OS with virtually same setup.
I can connect to TS3 by supplying RD Gateway Server Setting ( like the screenshot above. However if I change the computer name to TS1, it does not connect.
It says "The creditials that were used to connect to TS1 did not work. Please enter new credentials".
Both TS1 and TS3 are the same except TS1 is a licensing server.
I can connect to TS1 if I simply supply IP address in the Computer Name field and not choose  RD Gateway Server Setting because I have a port forwarding setup: 3390 is forwarded to TS1.
But if possible, I like all Terminal Servers accessible using RD Gateway Server Settings and just enter Terminal Server Netbios Names.
Can you help?
Who is Participating?

[Product update] Infrastructure Analysis Tool is now available with Business Accounts.Learn More

I wear a lot of hats...

"The solutions and answers provided on Experts Exchange have been extremely helpful to me over the last few years. I wear a lot of hats - Developer, Database Administrator, Help Desk, etc., so I know a lot of things but not a lot about one thing. Experts Exchange gives me answers from people who do know a lot about one thing, in a easy to use platform." -Todd S.

Thomas GrassiSystems AdministratorCommented:
Do you have your own DNS Server running locally?

If so create an A record for each server

test by pinging the name you created

If you can ping by name then RDP will find by name
sgleeAuthor Commented:
DNS ManagerPING TestI can ping TS1, TS2, TS3. They are all jointed  to DC1 which is Domain Controller.
FYI, TS1 (W2008), TS2 (W2012), TS3 (W2008). They are all joined to the SBS2011/DC.
Thomas GrassiSystems AdministratorCommented:
I found this article

It only shows using FQDN check it out.

Once they make the first connection it will remember the settings so should not be a problem with which ever method you use to connect.

Experts Exchange Solution brought to you by

Your issues matter to us.

Facing a tech roadblock? Get the help and guidance you need from experienced professionals who care. Ask your question anytime, anywhere, with no hassle.

Start your 7-day free trial
IT Pros Agree: AI and Machine Learning Key

We’d all like to think our company’s data is well protected, but when you ask IT professionals they admit the data probably is not as safe as it could be.

sgleeAuthor Commented:
I tried 3rd option - which is most probable cause.
But it did not make a difference.
I have two other Terminal Servers that I did not have to do anything in GPEDIT and I don't have any problem connecting to those Terminal Servers.
Thomas GrassiSystems AdministratorCommented:
what happens when you run nslookup ts1

Do this from server that is working
Do this from workstation also

Post results
sgleeAuthor Commented:
From DC1(SBS2011):

C:\Users\DomainAdmin>nslookup ts1
Server:  UnKnown
Address:  fe80::cb5e:8a:1d18:bf9a

Name:    ts1.DomainName.local

From TS2:

PS C:\Users\Domainadmin> nslookup ts1
Server:  dc1.DomainName.local

Name:    ts1.DomainName.local
From TS3:
Server:  dc1.DomainName.local

Name:    ts1.DomainName.local
Thomas GrassiSystems AdministratorCommented:
Ok so the servers seem to have dns working ok.

What about the workstations?

TS1 TS2 TS3 are your terminal servers and DC1 is your domain controller right?
sgleeAuthor Commented:
From Win7 Workstation:
C:\Users\maceykoadmin>nslookup ts1
Server:  dc1.DomainName.local

Name:    ts1.DomainName.local
TS1 TS2 TS3 are your terminal servers and DC1 is your domain controller right?  ---> Yes.

TS is the first and active Terminal Server.  In the past users have been connecting to TS1 by entering TS1 in their Remote Desktop program. From their home, they would use IP address of the network in Remote Desktop program - I setup port forwarding 3389 - to TS1 Internal IP address (
As I added TS2 and TS3, then I learned that, instead of creating more port forwarding 3390 & 3391 to TS2 and TS3, I could just use the name of the computers like TS1, TS2 as long as I use RD Gateway settings ( and install Remote Desktop Session Host and Remote Desktop Web Access roles on the Terminal Servers.

So now I can connect to TS2 and TS3 using RD Gateway settings, but I can't do the same on TS1.
Thomas GrassiSystems AdministratorCommented:
OK then on TS1 you do have the roles Remote Desktop Session Host and Remote Desktop Web Access installed?
sgleeAuthor Commented:
TS1 Role ServicesYes
Thomas GrassiSystems AdministratorCommented:
Can you take port forwarding off then maybe that is conflicting?
sgleeAuthor Commented:
let me try. I need to get users who are connecting from outside off the TS first. I will post the result.
sgleeAuthor Commented:
Login Error MessagePort Forwarding DisabledAfter disabling Port Fowarding of 3389, I tried, but the same error.
It looks like it is trying to connect to TS1, but credentials are wrong?
The same credentials work on TS2 and TS3. Something is missing, I feel.
Thomas GrassiSystems AdministratorCommented:
Ok what errors are in the event log for TS1 and the computer trying to connect.

Yes I agree something is missing trying to figure it out.
sgleeAuthor Commented:
Event Viewer - SYSEventViewer - APPI was just checking that too ... I don't see any errors directly related to "Login activity" in APPLICATIONS. A bunch of Quickbook errors because that is what they use. In the APP event section, I see a warning (first line) comes up sporadically. But in the past 30 minutes, I tried to log in multiple times, but don't see any error or waning about rejecting login attempts.
SYSTEM is virtually clean from all errors or warnings.
Thomas GrassiSystems AdministratorCommented:
This are windows 7 clients right?

Are they using the same credentials for mstsc as the logon to their computer with?
sgleeAuthor Commented:
Correct. They all have Win7 OS on their computers.
Yes they are using the same username/password.
sgleeAuthor Commented:
OK. Since internal users can connect to TS1 and users (when they go home) can connect to TS1 by IP address (port forwarding), we can say "Terminal Server Functionality" is there, right?
The only think that I can think of is RD Gateway functionality on TS1 that is different or not quite right compared to TS2 and TS3 even though installed roles are the same.

Is there a tool that we can use to test RD Gateway functionality on TS1 so that I can compare the result of that test against TS2 and TS3?
Thomas GrassiSystems AdministratorCommented:
Yes I would say your TS is working more than one way to skin a cat.

Here is what I found on the Gateway
sgleeAuthor Commented:
do you know how to generate SSL certificate for the RD Gateway server?
I don't know where it is because I have never generated one.
Thomas GrassiSystems AdministratorCommented:
This here are the steps required

Step 1
Step 2
Step 3

Take a look at them
sgleeAuthor Commented:
This is getting too complicated ...
sgleeAuthor Commented:
I got it. I don't know why but, to connect to TS1, I have to supply FQDN.
So instead of TS1, I entered  TS1.DomainName.local and it WORKED!!!
I don't understand why TS2 and TS3 worked w/o FQDN though.
I was able to connect to TS2 & 3 using FQDN as well.
Go figure!
Thomas GrassiSystems AdministratorCommented:
Yes FQN like I said in a prior post was the way to connect.

Yes it is very strange how FS2 & FS3 do not need FSQN

I would just make them do the same method

Glad I could have been help to you
sgleeAuthor Commented:
Yes you are correct. I just saw "FQDN" in your post ID: 38766995.
I don't understand why I did not pay attention to your previous post. I think I just clicked the link without paying attention to your actual comments along with the link.

Thank you for staying with me.
It's more than this solution.Get answers and train to solve all your tech problems - anytime, anywhere.Try it for free Edge Out The Competitionfor your dream job with proven skills and certifications.Get started today Stand Outas the employee with proven skills.Start learning today for free Move Your Career Forwardwith certification training in the latest technologies.Start your trial today
Windows Server 2008

From novice to tech pro — start learning today.