People post licensing questions constantly at SQLServerCentral about the various scenarios and situations they face with their SQL Server instance configuration. Many of the are fairly easy to answer, but more and more I read about environments that are complex. The problem is it is not clear what purchases are needed from the licensing documents.
Multiple cores, virtual environments, and the restrictions for different editions of SQL Server mean there are often no simple answers. I know Microsoft is trying to earn a profit and these days hardware advances complicate matters, but I do think that Microsoft can make this much easier to understand than it currently is.
There are lots of possible scenarios for systems, but publishing data on the Internet is easy. I don't understand why the licensing documents do not include 10 or 20 possible configurations for SQL Server environments and explain what the licensing requirements are for each one. I bet that there are even some developers at Microsoft that can build a way for anyone to submit their own scenario, get it added to the list, and an answer published. I would guess there might even be able to build a notification feature for the submitter.
It's easy to contact a Microsoft licensing representative, but many of these people aren't SQL Server experts, and often don't understand some of the implications of complex environments. What's worse is I have different friends getting different answers from Microsoft representatives. By not using published scenarios and licensing requirements, and depending on employees' interpretation of the documents, Microsoft is as likely to under charge as over charge customers. Neither situation is a fair one.
I don't mind paying for the software I use; I just want to know what the cost is before I architect a complex environment.
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