Microsoft licensing

Could anybody help me figure out the Microsoft licensing, please? I tried to read some stuff on their website but it was confusing....

I'm thinking of upgrading to Windows Server 2008 but I'm not sure what and how many licenses I need to buy. I have 10 servers to upgrade and 200 users that use these servers for file, printing, email, sql, etc.
Do I have to buy 10 Win 2008 licenses plus 200 device/user CALs?

Also, I have a terminal server to upgrade to 2008 and office 2007. This server is accessed by 20 people. How many licenses do I need to buy? Do I need license for win2008, CAL for Office and CAL for TS?

Any help would be appreciated!

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If you figure out MS licensing let me know:)

Can't speak to the T/S part of your question, but yes, you need to buy 10 Win 2008 licenses unless you purchased Software Assurance (SA) on the old server 2000's that you are running and have kept it up over the years.  As far as users, you either need to purchase user or device CALs depending on your setup.  For me, it made more sense to purchase device just depends on if users share PCs or not.  Again, if you purchased the appropriate number of CALs for 2000 server with SA and have kept the SA up to date, then you would be OK on the CALs.
These things are best sorted out in collaboration with your license reseller. They will be able to calculate which licence model is best for you in the long term (Open Licence, Enterpise Agreement, Software Assurance etc.) and how to comply with local legislation etc. to get the best deal. Also Microsoft is known to provide special deals for non-profit organizations, schools etc., maybe you are elegible for one of these programs.

In general terms:
"Do I have to buy 10 Win 2008 licenses plus 200 device/user CALs?"
"This server is accessed by 20 people. How many licenses do I need to buy"
20 (per user). If you have an office with 5 PC's and these 20 people take turns using the system, you only need 5 per-device.
"Do I need license for win2008, CAL for Office and CAL for TS"
yes, yes and yes.

Redwulf's statement about working with yourlicense vendor is right. Even though there are certain absolutes, like if you have 10 copies of server, you need 10 licenses, somethings are up in the air as we both have alluded to concerning CALs and the like.

Work with a reputable vendor but, use common sense as to your particular setup.

For example, MS keeps trying to get me to buy into their all encompassing license (Sorry don't remember the name) that includes all sorts of Office and server licenses...they say I will save money over buying separate.  However, when we start talking about what I actually do with my products as far as upgrading and the like it quickly becomes evident that going their way is waaaay more expensive than what I am doing. If I were in a scenario where I was upgrading wholesale across my company the OS and Office and my other products such as Exchange and SQL, then it would make sense to do what they suggest...however, I don't and my way ends up being much less expensive.  

So, work with your guy, but know where you're going over time so that you can make the best and most cost effective choices.
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