Get a written exit plan for your Windows Server 2016 estate, with a fixed price
Tell us the server count, the sites and the date that matters. We come back with the sequence (what is replaced, upgraded in place, moved to Azure or kept on ESU for a year), the licensing it triggers, and a fixed price for the work.
- 12 January 2027
- Windows Server 2016 leaves extended support. After that date it receives no security updates unless it is enrolled in Extended Security Updates, which Microsoft sells by the year or meters monthly through Azure Arc from 13 January 2027. Domain controllers and Hyper-V hosts on 2016 are the usual reason the date needs a plan rather than a patch window.
- $2,950 fixed, two weeks
- The Windows Server 2016 End of Support Assessment and Roadmap: every 2016 host found, a path and a cost line for each, the licensing it triggers, and a fixed quote for the work.
- Per-server prices, in writing
- Upgrade in place to Windows Server 2025: $650 per server plus a $1,950 tenant fee. ESU enrollment through Azure Arc: $35 per server plus $1,450. Several sites and many domain controllers: one multi-site engagement, from $12,500.
Four things on paper, before any work starts.
The plan is written for the person who has to defend it: to an acquirer, an auditor, a hardware budget or a hosting renewal. Each line carries a reason and a cost.
A decision for every server
Each Windows Server 2016 host gets one of four paths, written down with the reason: replace it, upgrade it in place to Windows Server 2025, move it to Azure, or keep it on Extended Security Updates for one year through Azure Arc because it will miss the date.
Domain controllers are replaced and promoted, not upgraded underneath a live directory. Failover clusters move one version at a time. The plan says which servers those rules catch.
The licensing line
Windows Server 2025 Standard or Datacenter at the 16-core minimum per server, and the CAL version rule: client access licenses must match or exceed the server version, so 2016-era CALs without Software Assurance mean a CAL refresh for every user or device.
Both are priced from the current Microsoft price list and shown beside our fees, so the licensing is not the line that surprises finance.
The domain-controller sequence for multi-site estates
Schema preparation first, Entra Connect moved off any domain controller that is retiring, then site by site: promote the Windows Server 2025 domain controller, demote the 2016 one, move its IP address and DNS name across, and check what still points at it.
Estates with several sites and many domain controllers are scoped as one multi-site engagement, from $12,500, rather than a stack of single-server upgrades.
A fixed price before any work starts
The Windows Server 2016 End of Support Assessment and Roadmap is $2,950, fixed, delivered in two weeks; you pay after you approve delivery.
The work it leads to is quoted the same way: the Windows Server 2016 to 2025 Upgrade Service at $650 per server plus a $1,950 tenant fee, and ESU enrollment through Azure Arc at $35 per server plus $1,450.
How the two weeks go.
Inventory call
Thirty minutes with the person who knows the estate: the server list as you have it, the sites, the hypervisors, where Entra Connect runs, and the date that matters.
Read-only discovery
We find every Windows Server 2016 host the network agrees exists, with its edition, core count, roles and what depends on it. Nothing is changed.
The written plan with the cost table
A path per server group, the sequence with dates set back from 12 January 2027, the licenses and CALs it triggers, and Microsoft's ESU or Azure charges beside our fees.
The fixed quote
One written price for the work the plan calls for, by service, before anything starts. Take it, or take the plan to whoever you like.
Nothing is ordered until a person at IT Partner confirms it with you. Microsoft's charges, ESU and Azure among them, are always billed by Microsoft.
Tell us about the estate.
Six answers and an optional note. A person reads it and replies within one business day with the plan outline and the assessment quote.
The answers, in the open, before you send anything.
Four articles and two calculators cover most of what the plan will say. Read them first if you would rather check our reasoning than take our word.
Windows Server 2016 end of support on 12 January 2027
What stops on the date, how ESU works for this generation (Azure no longer waives it), and the order of work.
Replacing Windows Server 2016 domain controllers: the order of operations
Schema preparation, the Entra Connect move, per-site promote, demote and re-IP, and the decommission checklist.
A 20-server estate: upgrade in place, Azure or ESU, the cost table
The three paths priced for a worked estate at Microsoft list prices and our fixed fees, and what the number leaves out.
The one server you cannot replace
ESU through Arc, a Windows IoT Enterprise LTSC rebuild, or isolation: the decision table for the box the vendor will not move.
ESU calculator
Extended Security Updates per year through Azure Arc or the annual channel, at Microsoft's list price, for the servers you name.
Windows Server calculator
Windows Server 2025 licenses and CALs for your cores, hosts and users, at Microsoft's list price.