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Server 2003 will no longer allow RD connections

I recently "activated" a Remote Desktop Services manager on our 2008 R2 DC. We have an application server that often times quires more than 2 users would try and connect to but the licenses were all in use - so I picked up an 5 additional licenses and installed them as noted on the above server.

Now however I'm unable to remote desktop into our 2003 app server at all. I've checked event logs on both servers and there doesn't seem to be anything wrong with either box. Under "terminal services configuration" on the app server under licensing it says "remote desktop for administration". There's no other option and to make any changes it says to do it through add/remove programs but doesn't really tell you want you need to change in there. From the 2008 Remote Desktop Services Manager I can add my app server which shows a green "up" arrow in the list on the left pane but in the right pane under "sessions" tab it shows a red "down" arrow - yet for state it says "Connected".

Am I missing something on my 2003 app server? Any suggestions on how I can correct this?
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ITGeneral
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ITGeneral
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1 Solution
 
Swamish NaikExpertCommented:
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arnoldCommented:
Based on your second paragraph, the 2003 was not configured as a terminal Server.
not sure whether the changes you made on the 2008 forced a change in GPO/GP preferences on the 2003 that might explain its behavior.

You would need to add terminal services to configure the 2003 as a terminal server.

There are steps that you have to pay attention to once the system is a terminal server i.e. should you want to install anything via the terminal or local login, you would be required to change the mode from exec to install.
(change user /install prior to attempting any install/uninstall etc.)

you could try using wmic to remotely disable remote desktop administration and reenabling it.
http://www.vedivi.com/support/blog/71-how-to-enable-remote-desktop-programmatically.html

Can you use the terminal services manager on the 2008 to connect to the 2003 to see what session there might be and reset/logoff the sessions that are present?
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ITGeneralAuthor Commented:
nikeswamish: thanks for the link - I'll keep it handy but I think my issue is really more "basic" than that.

arnold: You are correct, I do not have Terminals Server installed on the 2003 box. I was going to install it but when you do you get a scary message about any apps that are already installed on the server will no longer work. Very concerning considering this server is running our companies billing system. I don't recall seeing such a message previously (obviously its always been there) but just looking for some validation that this won't affect anything outside of terminal services.

I think what happened is that I was having issues getting the 5 licenses to work on this 2003 server so I probably uninstalled Terminal Services but it wanted a reboot to complete which I couldn't do at the time. I just got around to restarting that server a couple days ago at which point all this stuff started. (this is just more for history so you you guys know what went on).

So I guess my question then is once I get TS installed on this 2003 box can I then connect it to my 2008 Licensing box to get to the 5 additional licenses I purchased for this thing? I was led to believe that I could.
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arnoldCommented:
Terminal services at times requires a different type/class of software.
I.e. application licensing related items.  I think office is one of those.

The billing software functionality would depend on the billing software whether it can or can not function in a terminal server type environment.

Do you have terminal server related event log entries on the 2003 or on the 2008 that deal with license denial?
Buying CAL licenses does not enable a TS license, do you have a termianl Service license?
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ITGeneralAuthor Commented:
I don't see any events in either event viewer pertaining to TS licensing.

Check out the attached pictures for a better idea of how I've got things setup right now. At the moment I can't even Remote Desktop to my 2003 server but I think thats because I need to install Terminal Server on it. Just looking for a little "validation" as I don't want to break anything on that app server as the scary mesage in "TSMessage.jpg" seems to indicate. Currently nothing uses Terminal Services or Remote anything on that box. Again, I just want to leverage the 5 licenses on "RDHostServer.jpg" so that I can have users on the app server take advantage of them as opposed to just the traditional 2 Remote Desktop licenses.
RDHostServer.jpg
TSMessage.jpg
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arnoldCommented:
Once the server is marked as a terminal Server the operational mode will be execute.
You would need to change the mode to install to add/install applications.
Some applications are Terminal Server aware and have different licensing criteria.
i.e. when installed on a workstation the license is per workstation on a terminal server it will be based on the number of users who access the terminal services.
I think some products have a terminal services version.
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arnoldCommented:
Depending on which version of 2008 you have and whether hyper-v is an option for you to try and setup a VM windows 2003 TM and see how and what the interaction is between what you need to run on the existing 2003 and how it behaves on the VM 2003 TS.
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ITGeneralAuthor Commented:
Well, my end goal is still to get more than 2 concurrent users via Remote Desktop onto this server so my only question left is will making this thing a terminal server allow me to do that? Also, will I be "allowed" to connect a 2003 TS box to a 2008 Managing server w/2008 user CALs and have it assign those CALs to my 2003 TS box?
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arnoldCommented:
Yes, configuring a server as a terminal server will allow multiple user including non-administrators to access the system as long as they are members of the Remote Desktop Group.
Yes, you would need to properly license the system as a Terminal Server and add the necessary TS CALs
http://technet.microsoft.com/en-us/library/cc731629%28WS.10%29.aspx

You have to decide whether you want CALS per user or cals per device.
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ITGeneralAuthor Commented:
Sorry for the long wait - we ended up rolling this back so that its just accessible to the standard 2 remote desktop users. I would like to activate more at some point. Arnold asked the question "Buying CAL licenses does not enable a TS license, do you have a termianl Service license?" to which the answer is YES we do have a TS server but its a 2003 box. I was told that the 2008 CALs could be used on it and that they would work.
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arnoldCommented:
That is not the point, you need to license the 2008 for TS services.
http://technet.microsoft.com/en-us/library/cc754746%28WS.10%29.aspx

because you have a terminal services box on 2003 does not license the 2008 unless the 2003 is an SBS and the license extends.
CALs deal with number of users/devices that can use the TS which I believe has to be licensed separately.
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ITGeneralAuthor Commented:
So it looks like my problem was that I was trying to use a 2003 TS box to issue CALs to a 2008 box.
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arnoldCommented:
Not specifically, The issue is that it is a two step process. You license the TS server so it continues to work after the 90/120 days. The other deals with a DC or another server that will be issuing/handling the CALs for the Terminal Services.
You have the DC/server that was configured with CALs to allocate, you seem to not have had licensed the TS service on the 2008 server.
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ITGeneralAuthor Commented:
I'll try that first.
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