How many thousands of users?
I've run some TCP/IP client/server connection tests in the past on Windows 2003 Server and managed more than 70,000 connections on a reasonably low spec VM. (see here for details: http://www.lenholgate.com/archives/000564.html). I would be extremely surprised if Windows 2008 Server is limited to less than 2003 Server and, IMHO, the posting that Cloud links to is too vague to be much use.
Personally I'd test it and see. Even if there is no inherent limit in the Windows 2008 Server version that you intend to use there will still be practical limits based on memory, processor speed and server design.
If you want to run some 'generic' tests you can use my multi-client connection test and the associated echo server. Detailed here: http://www.lenholgate.com/archives/000568.html and here: http://www.lenholgate.com/archives/000569.html. These are what I used to run my own tests for my server framework and these are what allowed me to create 70,000 active connections on a Windows 2003 Server VM with 760MB of memory.
Edited to add details from the comment below...
If you're already thinking of multiple servers I'd take the following approach.
Use the free tools that I link
to and prove to yourself that you
can create a reasonable number of
connections onto your target OS
(beware of the Windows limits on
dynamic ports which may cause your
client connections to fail, search
for MAX_USER_PORT
).
during development regularly test your actual server with test
clients that can create connections
and actually 'do something' on the
server. This will help to prevent
you building the server in ways that
restrict its scalability