Windows licensing mess

Hello everyone, I need some help figuring out the Microsoft licensing mess.

I inherited a small network and I want to make sure I'm covered when coming to licenses. I know that I need license per processor and also user CALs. If I get a Datacenter license, do I have to get licenses for every VM(ex.  5 2012 Standard VMs)? Do I need 1 CAL per user/per server or just 1 user CAL for all accessed servers(ex, file server, database, print, etc). Also, can I apply 2008 user CALs towards a server that has been upgraded to 2012 or do I need to buy new CALs?

I feel like Microsoft tries to confuse customers on purpose. There's got to be a better way to get compliant.

Thank you so much for the help!
Alan DalaITAsked:
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Cliff GaliherCommented:
I actually think Microsoft has (finally) done a good job of cleaning up Windows Server licensing. They have a PDF brief that is pretty straightforward and doesn't require a legal degree to understand.

Second link on the right:

Now, with that said, ANY opinions here are not legally binding. Call Microsoft. Full stop. The "some guy told me this would be fine" is gonna cost you if "some guy" was wrong.

A datacenter license covers all VMs on that physical server for 2 processors. So your 5 VMs may be covered by one datacenter license, or may require 5. Depending on how many physical servers you have (spreading VMs around, clustering, etc) and how many processors they each have. You didn't really say.

A user CAL covers access to all servers of that version or lower for the assigned user. Same basic principle for device CALs. The device can access any server of that version or earlier. So one CAL covers multiple servers, as long as the server isn't newer than the CAL.

Which also answers your last question. 2008 CALs will not cover accessing 2012 servers. Period.
Alan DalaITAuthor Commented:
Thank you for your answer! What doesn't make sense to me is why doesn't Microsoft control this better. IT can install a server OS multiple times and if the licenses are not counted carefully, an organization can get out of compliance without even being aware of it. I find it hard to believe Microsoft can't control better who's installing what. I mean, I have 1 license of Win 2012, install it on 10 servers hoping that I don't get caught?! Don't they keep track of how many times one license is being used?

Sorry, I'm just venting but at the same time I want to know if I'm missing anything about the way Microsoft controls their software.

Again, thank you so much!
"I have 1 license of Win 2012, install it on 10 servers hoping that I don't get caught?! Don't they keep track of how many times one license is being used?"

If you post your use of one licence installed on 10 servers in public sites such as here, then Microsoft may notice you?

Take care.
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Alan DalaITAuthor Commented:
I'm not, I'm just giving an example. I'm not sure why you draw that conclusion. If you don't have insight into my question, why bother responding?

Cliff GaliherCommented:
Keys are bot the same thing as licenses. And when you get into processor based a single 4-proc server requites TWO licenses. Do you require a customer to enter two Keya before the server activates? Or what about virtualizations? Should a customer have to re-enter a key every time they configure replica or live migrate a VM? For each "they should do this" you introduce a burden on the IT PRo, and frankly also on MS to code that solution (require entering two keys, etc) so the cost goes up for the business and for Microsoft and nobody is happy. And that's if it all works! Troubleshooting when activation goes wrong (which key didn't work) is also a consideration.

My opinion is we are all big boys and girls. You can't tell the IRS (or other tax xollectng vody for your country) "you should track my profit so I don't have to." Or tell the government "I didn't know I had to have formal training *and* be certified to practice law/perform surgery/ claim to be an accountant.

It is a business's responsibility to stay in compliance with local laws, know their requirements for taxes, business licenses, etc, and stay legal. I pay a tax firm to file my taxes and they guarantee the filing. If I get fined because of an error thy made, they cover it. You can buy medical malpractice insurance. Many cities and states have mandatory background checks for business licenses. I.T. is *no* different. It is a profession. If you do it yourself, like filing hour own taxes, you take that burden. Or you hire someone, and make compliance part of the contract, and they, as professionals, take that burden.

Either way, I don't want MS doing something that complicated deployments technically and drives up costs. You, of course, and disagree and share your opinion with them via uservoice, etc.

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Alan DalaITAuthor Commented:
Seriously, it can't be that complicated but what do I know?

Thanks a bunch for your time and consideration.
re: "If you don't have insight into my question, why bother responding?"

You posted:
"I have 1 license of Win 2012, install it on 10 servers hoping that I don't get caught?!"

This is a statement... put "for example" in front if you do not wish to be misunderstood.
Alan DalaITAuthor Commented:
Will do. Obviously common sense doesn't always work.
Lee W, MVPTechnology and Business Process AdvisorCommented:
Microsoft is not trying to trick you any more than the government is when you file your taxes.  You are expected to be honest.  Microsoft assumes you are an honest person.  If certain things happen, your keys may be blocked... if those things are legitimate because of a legitimate reason, you can call and resolve the problem.  At the end of the day, Microsoft has decided they are not going to "force" you to be compliant, I BELIEVE, because they can't... there are too many scenarios that COULD result in a major problems if they did something like denied access or blocked something... so they assume you are good... and then every so often, they MAY audit you.  At this time you have to prove you own what you say you do.  That's where proper documentation comes in.
Alan DalaITAuthor Commented:
Thank you for your response. It's not about being a bad person, it's about a confusing situation that doesn't really make sense not to be solved It's about the danger of turning a human error into a disaster.

Thank you all for your responses.
Mohammed KhawajaManager - Infrastructure:  Information TechnologyCommented:
Here is a brief rule of thumb for Windows Server:

1.  Data Center Edition is licensed per processor with minimum of two processors per host.  With this license, you could run unlimited number of VMs.
2.  Standard Edition allows 2 VM per virtualized host and each additional VM must be licensed
3.  Server licenses has no bearings on user CALs.  Each user needs a CAL
4.  Evaluate in your environment as to what license model fits the best (i.e. you are a manufacturer and there are multiple users on shift share a computer then device CALs would be cheaper whereas user CALs would be cheaper if you have users who use multiple devices to connect)
5.  Server and user CALs do not cover Remote Desktop CALs which is separate and again, user and device CALs model apply

With databases, below is generally a good guideline:

1.  Core licenses (minimum 4 cores per server) does not require you to purchase user CALs (again, do your homework as to what is cheapest)
2.  In a virtualized environment in order to migrate VM to different hosts at will requires you to have Software Assurance for your OS and SQL (otherwise you are limited to migrate once every 60 days after you call Microsoft)
3.  With all SQL versions and licensing models, you can implement multiple instances on same Windows host
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Windows Server 2012

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