SBS 2008 multiple Remote Desktop Session

This is one of several question on the same configuration, all share the same configuration:


First, we have a need for a remote office location to connect with our central office.  The remote location is inside of a "high security" environment which is very tightly controlled.  We were offered a Guest Wifi network which was to unstable to support the SSL VPN connection to our firewall (ZyXel USG100).  We are using the ZyXel which worked pretty well for most things, and we were able to establish several home to office VPN connections which although slow, were fully functional.  However, those same connections were not stable or satisfactory from the specific Remote Office location.  So, we were able to work through the bureaucracy to get them to allow the installation of the ZyXel SSL VPN client on the local network.  We were initially planning to connect to the ZyXel via its SSL VPN client then Remote Desktop to the client machines in the office which we needed to work on.

Initially things looked good but then it all fell apart  - remote desktop does not behave properly.  We can only remote desktop to the SBS 2008 server which operates as the networks DHCP, DNS, IIS, application server, and database server.  We can RD to it only via the IP address, although we can ping the server via the fully qualified domain name, but RD will not connect to it via FQDN only via IP.  Further, we can ping the various clients via IP or FQDN but neither will connect through RD.  We can however connect to them if we go through the SBS 2008 server and use terminal services or RD from the server to the client machines.

The landlord of the Remote Office will not allow us to use native Windows tools like PPTP to connect to our SBS 2008 server, which does not seem to have any of these problems, at least when used from our private home networks.


If we have to live with things the way they are, we need to have at least three Remote Desktop sessions to the SBS 2008 server so that we can then go to different clients through Terminal Services.  Right now, we can get two Remote Desktop sessions going as long as no one is logged into the server directly which is not a problem.  Is there a way to over come the two user limit?
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For administrative RDP you are given two licenses to get more than two you have to purchase terminal server licenses and set it up as a terminal server.
OldLinuxGuyAuthor Commented:
That would be true if they are both administrators.  I did not set them up that way, however, I will check to be sure that they are still just users.

Does this hold with normal users as well?

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The system will only allow two connections, while in administrative mode. The connections can be users or admins but you only get two without purchasing licenses and adding the terminal server role.
Cliff GaliherCommented:
This is SBS. SBS *CANNOT* run as a TS/RDS server, even with licenses. You will need to packet trace and find out why you cannot RDP to other machines. Alternatively, you could use RWW which would not require a VPN and should sidestep network routing issues.


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Unfortunately cgaliher is correct.

erminal Services and Windows Small Business Server 2008
Review the following guidelines before you configure Terminal Services with Windows SBS 2008:

Use the second server that is included with Windows SBS 2008 Premium for Terminal Services. You cannot use a server that is running Windows SBS 2008 as a terminal server. Terminal Services does not coexist well with the rest of the applications and services that are included with Windows SBS 2008.

For the terminal server, you can use either the second server that is included with Windows SBS 2008 Premium or Windows Server 2008 Standard with a separate server license.

Terminal Services CALs are required for each user or device that accesses or uses the server software. Terminal Services CALs are not included with the Windows SBS 2008 server license or the Windows SBS 2008 CALs. You must purchase Terminal Services CALs separately.
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