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Windows licensing with regards to 2000 DC / 2003 TS , vpn and web

Licensing question one: How many user cals are needed and how many TS cals are needed to implement a terminal server in the follow setup.


1 - windows 2000 server serving files and printing (already established)
1 - windows 2008 server running terminal services (application mode) (to be built)
20 - in-house users (accessing files shared by w2k) (already own 30 cals)
10 - remote users for accessing application installed on the 2008 box (to be purchased)

Because users are accessing an application on the win2003 server but files on the win2000 server are win2003 cals needed?

Which would I need:
a) 30  windows 2000 cals + 10 ts cals
b) 20 windows 2000 cals + 10 win2008 cals and 10 ts cals
c) 30 win2008 cals and 10 ts cals

Second question, from my understanding XP comes with a built in TS cal for access remote servers. Does this only apply to accessing a win2000 terminal server or any version?

Third question on vpn.  If as MS server is doing VPN authentication are there additional licenses need specifically for VPN or do the user CALS cover that?

Fourth question on web site authentication.  From what I understand if I use IIS and authenticate (think sharepoint services) I need another special license for that, like a external connector.  Is this correct?  What if I use a different solution like joomla that use ldap to authenticate users, do I need MS licenses for this?  

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Darius Ghassem
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First thing no one on EE is qualified to answer questions about licensing you should contact the licenser which is MS in the situation about any questions on their licensing. If you were audited by MS and you stated that the licensing information received was from EE you would not have a leg to stand on.

Now with that said. You need to have TS CALs for any user or device connecting to a TS server. You don't get a free TS license with an RDP client.
If any user connects to the server for any service including authentication you need to CAL.
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dariusq- your are correct that xp didn't come with a ts cal but ms didn't require one when connecting to a win2000 server however TSCALS were not needed (maybe there were not even around then?).  I found my answer to his issue at note the "changed to windows server 2003" section. (QUESTION 2 answered)

 "If any user connects to the server for any service including authentication you need to CAL."

Is it in your belief that this is true in the event of using AD LDAP for Joomla authentication? (even though no the user doesn't connect to the server and doesn't access information from the server)

As for contacting a license vendor am leery about this because 1) I have contacted one before and could not get a straight answer and 2) from the dozens of posts I have read a MS rep doesn't necessarily know the answer.  Many people have received different answers from different ms reps on the same issue (or so they say).  Once I have a feel for what I think the correct answer is I will ask MS and if they confirm it then I am good.  

I am not saying the anyone on EE is or is not "qualified" but I am sure that their are people out there that have had a similar situation or a grasp on MS licensing.   I am not a licensed electrical contractor but I am certainly capable of installing an electrical outlet in my house according to code.  Just like someone may not be "qualified" from an MS certification perspective that doesn't make them any less knowledgeable.  
Yes, but again if you get an answer from MS even if wrong if you were audited you can then present this information to them you would not be able to present the EE information at all.

MS should give you a close enough answer to the questions there might be a couple of out of whack things but usually you get a 95% correct answer on licensing.

If a service connects to AD for authentication then you need a CAL from my understanding. The Joolma authenitcation service is still contacting AD to authenticate a user.

We might have a grasp of licensing but we still don't speak on behalf of the licenser so we must state this information in our posts. Kind of like a disclaimer. Also, every licensing situation is different like yours for an example.

Windows 2000 Server did require TS CALs to access the server in Application Mode. You had two free connections using Remote Admin Mode which is the same when using 2003 and 2008 server but instead is called Remote Desktop.
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Darius Ghassem
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Thanks for the link.  This definitely answers some of my questions.