Windows Server and SQL Server Licensing and True-Up Advisory

Under an Enterprise Agreement you can add users, devices, products and servers during the year without individual purchase orders, and the additions are reconciled and paid at each enrollment anniversary — that reconciliation is the true-up. Prepared badly, it is either an over-count you pay for or an under-count that surfaces in a later licensing review with back-charges attached. This engagement establishes the actual position from inventory and entitlement evidence before the anniversary, so the order you place is right-sized in both directions and every line has arithmetic behind it.

A server licensing inventory workbook; an entitlement register with proof sources across Enterprise Agreement, Open Value, CSP, OEM and retail; the compliant per-core or Server + CAL and edition position for every host and VM with the core-count math shown; a Software Assurance renewal decision memo; an Azure Hybrid Benefit and License Mobility map against your Azure or Azure Local plans; an Extended Security Update eligibility matrix for every Windows Server 2012 R2, 2016 and SQL Server 2016 instance; an Azure Arc pay-as-you-go comparison; the right-sized true-up or renewal order by SKU and quantity; a savings-and-exposure memo; and a walkthrough with the engineer who did the work.

$1,950 per project, fixed and quoted in writing before work begins; you pay after you approve delivery. The fixed price covers one agreement family and an estate of up to 50 Windows Server instances and 20 SQL Server instances. Larger estates, multiple agreements, subsidiaries or regions are quoted per estate. Microsoft's license prices, Software Assurance fees, Extended Security Update charges and Azure consumption are billed to you by Microsoft or your reseller, not through this fee.

One week of our work: kickoff and evidence on day one, inventory and entitlement reconciliation through day two, core counting and edition analysis through day four, the Software Assurance, Hybrid Benefit, ESU and Arc decisions through day five, and the order, memo and walkthrough on day five. The calendar moves only if inventory exports or entitlement records arrive late, so gather them before kickoff.

By rule first, then by price. Server + CAL exists for SQL Server Standard edition only, and it requires a CAL for every user or device that connects, directly or through middleware — so if the population cannot be counted, as with a public website or an application tier serving the public, per-core is the only compliant model. Where the users can be counted, we cost both: a small internal application with thirty known users is usually cheaper on Server + CAL, a sixteen-core public workload is per-core by definition. Windows Server is per-core with CALs in every case. Our SQL Server licensing calculator shows the comparison for one machine; the engagement does it for every instance with your entitlements alongside.

Against Microsoft's minimums and the hosts a VM can actually land on. Windows Server needs at least 8 core licenses per physical processor and 16 per host; Standard covers two virtual machines per full set of host licenses and stacks for more, while Datacenter covers unlimited VMs on the licensed host — so a dense cluster tips to Datacenter and a lightly loaded host stays on Standard. With active Software Assurance or subscription licenses Microsoft also allows licensing by virtual machine at a minimum of eight core licenses per VM, which can beat host licensing when VMs are few. SQL Server is licensed per core with a four-core minimum per VM, or every physical core on the host with Software Assurance or a subscription if you want Enterprise's unlimited virtualization. Because a VM that can migrate between hosts must be licensed on each host it can reach, cluster membership is part of the arithmetic, not a footnote.

Only where you will use what it buys, and the memo answers that per product family rather than for the estate as a whole. Software Assurance on Windows Server and SQL Server gives you new version rights — the path to Windows Server 2025 and SQL Server 2025 — Azure Hybrid Benefit, License Mobility for SQL Server, licensing by virtual machine, and the Software Assurance that Microsoft's Volume Licensing route to Extended Security Updates requires. On a host you will migrate to Azure next year that is worth a great deal; on a server you will retire before the term ends it is money for nothing. The memo prices renewing, dropping and converting to subscription licenses for each family so procurement is choosing between numbers.

You apply SQL Server core licenses with active Software Assurance or subscription to Azure instead of paying the license-included rate. For Azure SQL Managed Instance and Azure SQL Database, Microsoft's published conversion is one Enterprise core license for four General Purpose vCores or one Business Critical vCore, and one Standard core license for one General Purpose vCore; for SQL Server on an Azure VM the licenses cover the VM's cores subject to the four-core minimum. Microsoft allows a 180-day migration allowance during which the same licenses may run on-premises and in Azure, after which they may be used only in Azure. The map in the engagement tells you which licenses qualify, what they cover, and when the allowance runs out against your migration plan — and our SQL Server to Azure Migration Assessment picks up the migration itself.

It depends on the channel each license came through, which is why the matrix is per server. Per Microsoft's product lifecycle, SQL Server 2016 extended support ended on 14 July 2026 — it is out of support now — and Windows Server 2016 extended support ends on 12 January 2027. Microsoft's documentation makes ESU for SQL Server 2014 and 2016 available for up to three years after support ends, so SQL Server 2016 coverage runs to July 2029, through Volume Licensing with Software Assurance or by connecting instances to Azure Arc with pay-as-you-go billing — which Microsoft states needs no Software Assurance — and, unlike SQL Server 2014, SQL Server 2016 does not receive free ESU simply by running on an Azure VM. For Windows Server, Microsoft's documentation ties ESU purchase for on-premises and Azure Arc-enabled servers to Software Assurance under a Volume Licensing agreement, while Azure VMs receive ESU at no extra charge; whether Windows Server 2016 follows the same terms as 2012 R2 is confirmed against Microsoft's lifecycle documentation at delivery. The matrix names the route for each server and the licensing gap that must be closed first. The server-by-server roadmap that follows — upgrade, migrate, ESU or retire — is the Windows Server 2016 End of Support Assessment and Roadmap and the SQL Server 2016 End of Support Options Assessment; this engagement supplies the licensing position those roadmaps are priced on.

Often not through the traditional route. Microsoft's Windows Server ESU documentation requires Software Assurance under a Volume Licensing agreement to purchase ESU for on-premises servers, and OEM and retail licenses without Software Assurance generally have no Volume Licensing route. The realistic options are then to bring the server under a qualifying license, move the workload to an Azure VM where ESU is provided at no extra charge, or upgrade — and for SQL Server 2016 specifically, Azure Arc with pay-as-you-go billing is the route Microsoft documents as not requiring Software Assurance. The matrix tells you, per server, which of these applies and what it costs, and we confirm the channel rules against Microsoft's terms in force when you enroll.

When the server's remaining life is short or its load is uneven. Windows Server pay-as-you-go through Azure Arc applies to Windows Server 2025 Standard and Datacenter, is billed hourly to your Azure subscription, cannot coexist with an OEM, retail or Volume License activation on the same device, and does not support Automatic Virtual Machine Activation — every VM carries its own license. SQL Server pay-as-you-go through Arc meters every core visible to the operating system, with a four-core minimum, whenever SQL Server is running. Over a five-year life on a stable host that arithmetic usually favors buying; for a server you will migrate within eighteen months, a seasonal workload, or a lab that is off most of the year, pay-as-you-go often wins. The comparison is done per candidate server, and connecting the servers is the Azure Arc Hybrid Server Management Implementation.

Yes, if you want us to — and the order is written so you do not have to. As a direct-bill CSP partner we sell perpetual Windows Server and SQL Server licenses, CALs and Extended Security Updates at Microsoft's published list prices; our margin comes from Microsoft, not from a markup on you, and nobody here earns a commission on your order. Customers who buy their Microsoft licensing through IT Partner also get break-fix support during business hours at no extra charge. Enterprise Agreement lines are placed through your EA and its Licensing Solution Partner, and the order says which lines belong where.

The no-charge Microsoft Volume Licensing consultation helps you choose a licensing program before a purchase — a conversation, not an inventory. The Microsoft 365 License Audit and Optimization is the same $1,950 audit tier applied to Microsoft 365 seats and service plans. This engagement is the server-estate tier: inventory against entitlements, core counting on virtualized hosts, Software Assurance, Hybrid Benefit, ESU and Arc decisions, and a true-up order. If your servers are few and the question is simply which program to buy through, start with the free consultation and we will tell you if this one is warranted.

No, and tell us at kickoff if you have. If a Microsoft licensing review or a Software Asset Management engagement is already under way, the sequencing and the disclosure strategy belong with your counsel and a SAM specialist, and this engagement is scoped as preparation, not representation. Where no review is pending, establishing your position now is the preparation a review actually tests: a documented inventory, an entitlement register with proof, and a closed gap list are exactly what a review asks for.

Then the memo says so, with the cost to close each gap and the cheapest compliant way to do it — which is often not the way the shortfall first appears. A cluster short on Standard licenses may be cheaper to fix with Datacenter; an Enterprise instance whose workload fits SQL Server 2025 Standard's limits — the lesser of four sockets or 32 cores, and 256 GB of buffer pool memory — may not need Enterprise at all; a server due for retirement may be better on Azure Arc pay-as-you-go than on a perpetual license. Nothing is bought during the engagement, and you decide what to close and when.

Yes, as far as the licensing goes. Azure Hybrid Benefit for Azure Local and the Windows Server licensing options Microsoft attaches to it are part of the map, and for third-party hosters the analysis covers License Mobility through Software Assurance for SQL Server — with the License Verification Form Microsoft requires within ten days of deployment — and the fact that Windows Server is excluded from License Mobility under Microsoft's program terms, so it must be provided by the hoster. Microsoft's Flexible Virtualization Benefit for licenses with active Software Assurance or a subscription is applied where your hoster qualifies; we confirm each hoster's status against Microsoft's Product Terms at delivery rather than assume it.