Windows Server 2016 ESU is billed from 12 January, whenever you buy it
Windows Server 2016 leaves support on 12 January 2027, 104 days from now. Everyone repeats that; the Azure Arc billing page, less so: licences provisioned after that date are back-billed to 12 January, the charge appears as a separate line item, deactivating and reactivating does not avoid it, deleting and recreating does not either, and Microsoft writes that "there are no conditions under which it can be avoided". Deferring stops being free. And before the price comes eligibility, which is where many smaller companies fall out: on-premises ESU requires Software Assurance or an equivalent Server Subscription, SPLA is not available for 2016, neither is the Visual Studio benefit, and transitioning from Volume Licensing is not supported with Azure Arc. Also: why the bill is decided by how you count cores —16 physical per machine or 8 virtual per VM, with Microsoft's own 1,024-versus-506-core example—, what to ask your CSP now that no list price has been published, and the option that is not on the slide.