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If I have one Windows Server 2003 Terminal Server and 200 TS-CAL:s (per Device), how many simultaneous connections can users make from those devices to this Terminal Server?

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This depends on your hardware> mostly Memory. We try not to go higher than 30 users per server on an 6-8GB RAM server. It will also depend on the type of applications being used. You might want to look at adding more servers for load balancing. You might need to do prior testing before actual production. Microsoft had some ways of accomplishing this in 2003, I'll need to find some documentation for 2008.

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