Windows 2008 r2 Terminal Services administration

I've got a client with a two small, three person offices.  He just bought a Windows 2008 R2 server and was hoping to have one of the offices connect into the server with the two Administrative Terminal services accounts occasionally.  He previously had a Windows 2003 server which allowed this, but when a second person attempts to connect into the new 2008 server, it kicks the first remote desktop session off.  Is there only one administrative terminal services "client" now in 2008 server?

I realize this is not how it was intended to be used, but the limited use of this feature for his employees worked well in the past with the 2003 server.  This new 2008 server is doing no "serving" of anything (no AD, no DNS, no DHCP, no file sharing), other than hosting a small software package geared towards his industry.  The server is basically a glorified workstation that allows more connections than a Windows 7 computer.  He is willing to buy Terminal server CALS, but we are not sure if Microsoft still sells them for Server 2008 r2.  And, if they do still sell them, can you buy just two cals or do you have to get a minimum 5 pack?  Can the server stay in a basic workstation/workgroup role and have Terminal services and cals installed?

Thanks for any help
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David Johnson, CD, MVPOwnerCommented:
They MUST be logged in to different accounts if it is the same account then yes the older one will get kicked.
Lee W, MVPTechnology and Business Process AdvisorCommented:
Unfortunately, your client didn't ask you first or post such a question here.

It's pretty much wasted money for his purposes.  The Administrative connections are for just that - administration, not end user connections.

If they purchased 2008 R2 as a volume license and NOT pre-installed on the server, then they'd have a volume license agreement active and that would allow them to order individual licenses for RDS.  Otherwise, I think you're stuck since I believe RDS licenses are VL only and you need a minimum of 5 OR a full server product to open an agreement if memory serves.

Really the best solution for this environment would seem to be Multipoint server, not Windows Server.  The low end Multipoint system would support up to 10 concurrent users, is cheaper than server (it does require CALs).  It also offers a few other features that could be quite useful that standard server does not.
Chris HInfrastructure ManagerCommented:
Dude, buy a 5 pack of 2012 TS cals.  They're backwards compatible
Spike99On-Site IT TechnicianCommented:
By default, Server 2008 won't allow more than one session per user account.  If you are ok with just the two admin accounts connecting, I don't think you need to buy the TS CALs.  The solution would be to either create a second account for the second user or to enable multiple sessions per account.

This page has some screenshots of how to enable multiple sessions per account in Server 2008 R2:

Personally, I'd go with creating a 2nd account for the 2nd user to avoid the possibility of creating profile issues (2008 is much less forgiving when it comes to user profiles than 2003 was).

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jbobstAuthor Commented:
Thanks for all the help
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