You need 250+ users for Software Assurance through Enterprise Licensing programs: http://download.microsoft.com/download/1/F/5/1F5357DD-F7C8-4CC8-8C5F-7F6B1569E

You need 250+ users for Software Assurance through Enterprise Licensing programs: http://download.microsoft.com/download/1/F/5/1F5357DD-F7C8-4CC8-8C5F-7F6B1569ECF0/Transactional_Licensing_Comparison_Chart.pdf http://download.microsoft.com/download/1/F/5/1F5357DD-F7C8-4... However, through the MOSP (for 5-250, now called "Microsoft Online Services"), you can get Windows Intune with Software Assurance for Windows for $11/user (at least when it was announced), which includes Software Assurance, which then includes a copy of Windows 10 Enterprise (to upgrade/install on PCs for licensed users) as well as management tools. There's a way to add Office 365 on a per-user basis to your Intune subscription as well, as long as you maintain annual commitments (or some gibberish like that). I'm not entirely clear on the details, this is why Microsoft usually has folks call in for pricing and such. But I hear it's easy to manage. There's two methods of enterprise/education licensing, per user and per machine. Home/Pro are sold per-machine only, with varying features. See license agreements for details ;-) Ultimately, you can disable most/all of the Windows 10 spying yourself without special editions of Windows, they just make it easier for folks paying the big bucks.