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Daniel WilsonFlag for United States of America

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Which Windows Server edition should I select for a public web server?

I'm looking at putting in some Windows Server 2012 machines for a large web application.  The team likes .Net, so we're pricing that option.

Which edition of Windows Server should I look at?  I'm thinking Standard, but is there a licensing problem if, for example, we have 5000 concurrent connections to the website?

DB server is separate, so not part of this question.  

Thanks!
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Brad Groux
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Thanks for the quick response, Brad.

Do I need server license + CAL's?  Or just a server license?
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Cliff Galiher
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Thanks for the correction on Datacenter naming Cliff, old habits die hard!

This website explains CALs pretty clearly - http://www.microsoft.com/licensing/about-licensing/client-access-license.aspx
Thanks!
It should also be noted that licensing advice from EE should never be considered trustworthy or legally binding. If you follow particular advice and get stung, the "I was told it was okay from a guy on EE" excuse won't save you. You realm should call MS pre-sales and get something in writing.
Good point, Cliff.  I'm getting close enough for ballpark pricing at this point. :)
The problem with Microsoft licensing is that you can ask 10 different MS reps and get 10 different answers, so definitely take a better safe than sorry approach. Thankfully, Server 2012 made it MUCH easier than the past.

As a good rule of thumb, always have a standard CAL for all of your users and a license for all of your production servers and DR servers and you should be good to go. But certainly consult your licensing reps from either Microsoft or third parties like CDW.