These CALs are like blanket licenses that cover any applicable connections in your organization. The short of it is that your Server CALs and RDS CALs aren't tied to a specific server. If office is on the RD server, as stated above, a license which has network usage product rights (volume for sure, I think OEM, but I think not retail) must be allocated for each device connecting to it office doesn't necessarily have to be installed ( think Windows CE thin client, etc.) ( EDIT: Yeah, they don't appear to be concurrent, so you would still need 100 RDS User CALs, but each CAL allows access to any and all RD Servers) 3- no active directory or any other service. 2- more than 2 users will be connected at the same time. What I am looking for: 1- a couple of users will use remote desktop to the server (4-5 users). If you have 100 users, 5 RD servers, but only 50 users will ever be on the various RD servers at any one time (either 10 per server, or 25 on 2 servers) you will - my understanding is - only need 50 RDS user CALs. I have an application that will be installed on this server, and it will host a file that acts like a database. So if you have 100 users and 20 servers mixed 2003/2008, you only need 100 user CALs for server 2008 (or 2012). Regarding the server user cals each user cal allows one user to connect to any and all servers of that version of OS and lower.
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