Know what to do with each 2016 server before 12 January 2027
Microsoft ends support for every edition of Windows Server 2016 on 12 January 2027, and the January 2027 security update is the last one. Server 2016 Exit Plan inventories each server's roles and applications, checks them against Microsoft's upgrade and migration rules, and gives you a written plan per server: upgrade in place, migrate to new hardware or Azure, buy Extended Security Updates, or retire it.
Updated
- A read-only inventory script lists roles, features, installed applications, domain controller and cluster status, so the plan starts from facts, not guesses.
- Each server gets one recommended path with Microsoft's supported upgrade route, the licences it needs and the risks we found, such as Essentials features that end with no direct replacement.
- A fixed price per server, paid once. The plan is yours to carry out in-house or hand to any IT provider.
Windows Server 2016 reaches end of updates on 12 January 2027, in all editions; the January 2027 Windows security update is the last update available.
Source: learn.microsoft.comMicrosoft support for Windows Server 2016 Essentials features, including Remote Web Access, ends on the same date; ESU is offered for the Standard and Datacenter editions.
Source: learn.microsoft.comWindows Server 2025 Standard lists at $1,176 (US MSRP) for 16 core licences, and CALs are required for every user or device accessing the server.
Source: microsoft.comWindows Server 2016 gets its last security update in January
Windows Server 2016 reaches end of support on 12 January 2027 in all editions: Datacenter, Essentials, MultiPoint Premium and Standard. Microsoft says the January 2027 security update will be the last one available. The server keeps running after that, but gets no fixes for new vulnerabilities, and Microsoft support for Essentials features such as Remote Web Access ends on the same date.
Many 2016 servers do one quiet job: domain controller, file server, line-of-business database or Remote Desktop host. The right path depends on that job. Windows Server 2016 can upgrade in place to 2019, 2022 or 2025 from installation media, but domain controllers, clusters and some roles have their own rules, Storage Server editions cannot be upgraded in place, and every Windows Server upgrade needs its own licence.
Extended Security Updates can buy time for Standard and Datacenter editions, not Essentials. Through Azure Arc, Microsoft's price list has 2016 ESU at about $5.21 per core a month for Standard, with a 16-core minimum per physical server, billed from 13 January 2027, and moving the server into Azure no longer makes ESU free. A short written plan per server is how you choose between upgrading, moving and paying for time.
Without it
- Doing it yourself: Free, and Microsoft documents the supported upgrade paths, the restrictions and the role migration guides, and offers…
- Extended Security Updates: Security updates from 12 January 2027 through January 2030, for Standard and Datacenter only, with Software Assurance,…
- Moving the server to Azure: Free ESU in Azure was a Windows Server 2012 benefit. For 2016, Microsoft's price list bills ESU on Azure VMs at the…
With Server 2016 Exit Plan
- A read-only inventory script lists roles, features, installed applications, domain controller and cluster status, so the plan starts from facts, not guesses.
- Each server gets one recommended path with Microsoft's supported upgrade route, the licences it needs and the risks we found, such as Essentials features that end with no direct replacement.
- A fixed price per server, paid once. The plan is yours to carry out in-house or hand to any IT provider.
- Role and application inventory
- Upgrade path check
How it works
- 1
Run the inventory
We send a read-only PowerShell script for each server. It lists roles and features, installed applications, services, domain controller and cluster status, edition, hardware and disk use, and changes nothing. You send us the output.
- 2
We check each server
Against Microsoft's supported in-place upgrade paths and restrictions, the role migration guidance, your applications' vendor support, and the licences and CALs the target version needs.
- 3
You get the plan
Within 3 business days: per server, the recommended path, the steps in order, backups and rollback, licence or ESU lines to budget, and the risks we found. One document you can act on or forward.
- 4
Questions answered
We answer follow-up questions on the plan by email for 30 days, and on the Small site plan in a 30-minute review call.
Features
Role and application inventory
Every role, feature, service and installed program on the server, so nothing is discovered for the first time on upgrade night.
Upgrade path check
Microsoft's supported in-place routes from 2016 to 2019, 2022 or 2025, and the restrictions that block them, such as language changes, Server Core to Desktop Experience switches, NIC Teaming or Storage Server editions.
Domain controller plan
Domain controllers get a step-by-step plan for adding a new controller and retiring the old one, instead of a blind in-place upgrade.
Essentials replacement
For Windows Server 2016 Essentials, a map of what it does for you today, such as Remote Web Access, and what replaces each function after 12 January 2027.
Licence and ESU lines
Core and CAL counts for the target version, and where ESU makes sense, the eligibility conditions Microsoft sets, such as Software Assurance or subscription licences.
Remote Desktop hosts flagged
Microsoft 365 Apps support on Windows Server 2016 ended on 14 October 2025, with security updates to 10 October 2028. Remote Desktop servers running Office get their own line in the plan.
Runbook per server
Backups first, then the steps in order, test points and a rollback path, written for whoever will do the work.
A look inside
What you get: the working view and the delivery report.
Illustration of the layout, built from this page's own feature list. It shows no real results.
Who it's for
Small businesses with one or two servers
A server in a cupboard that runs the domain, the files and an accounting database, set up years ago by someone who has moved on.
Schools, clinics and charities
Essentials or Standard servers on tight budgets, where knowing whether to upgrade, move or pay for ESU matters more than any one tool.
IT providers and MSPs
A list of client servers on 2016 and less than three months to deal with them. Get the inventory and plans done, and keep the upgrade work for your team.
Works with
- Windows Server 2016 Standard, Datacenter and Essentials
- Windows Server 2019, 2022 and 2025
- Active Directory Domain Services
- File and Storage Services, Remote Desktop Services
- Hyper-V and other virtualized servers
- Azure virtual machines and Azure Arc
- Read-only PowerShell inventory script
- Microsoft 365 Apps on Remote Desktop hosts
Pricing
One-time prices, paid once after we confirm the server count. You get a written plan and runbook; carrying out the upgrade or migration is not included, and new Windows Server licences, CALs or ESU are bought by you at Microsoft's or your reseller's prices. Founding customer pricing applies to early-access orders.
Orders are subject to the Server 2016 Exit Plan terms.
One server
$199 one-time
A single Windows Server 2016 machine
- Read-only inventory script
- Recommended path with reasons
- Step-by-step runbook with rollback
- Licence, CAL and ESU lines to budget
- Email questions for 30 days
Small site
$449 one-time
Up to 5 servers, including the domain controllers
- Up to 5 servers
- Everything in One server
- Order of work across servers
- Domain controller replacement plan
- Essentials replacement map
- 30-minute review call
MSP pack
$990 one-time
IT providers with 2016 servers across several clients
- Up to 15 servers across any clients
- Everything in Small site
- Plans under your brand
- One summary sheet per client
- Extra servers at $59 each
Compared with the alternatives
- Doing it yourself
- Free, and Microsoft documents the supported upgrade paths, the restrictions and the role migration guides, and offers a free 180-day evaluation of Windows Server 2025. The time goes into the inventory and the judgement calls, which is what the plan covers.
- Extended Security Updates
- Security updates from 12 January 2027 through January 2030, for Standard and Datacenter only, with Software Assurance, a server subscription or SPLA. Through Azure Arc, about $5.21 per core a month for Standard (16-core minimum per physical server). Time to move, not a destination.
- Moving the server to Azure
- Free ESU in Azure was a Windows Server 2012 benefit. For 2016, Microsoft's price list bills ESU on Azure VMs at the same $0.007132 per vCPU-hour, so a move to Azure means paying for ESU and the Azure resources.
- Your IT provider
- Often the right people to do the work. Ask for a fixed price per server, or hand them the plan so the quote starts from the same facts.
What changed
- Windows Server 2016 reaches end of updates on 12 January 2027, in all editions; the January 2027 Windows security update is the last update available. Source: learn.microsoft.com
- Microsoft support for Windows Server 2016 Essentials features, including Remote Web Access, ends on the same date; ESU is offered for the Standard and Datacenter editions. Source: learn.microsoft.com
- Windows Server 2025 Standard lists at $1,176 (US MSRP) for 16 core licences, and CALs are required for every user or device accessing the server. Source: microsoft.com
- Windows Server 2016 Standard ESU through Azure Arc is listed at $0.007132 per core per hour (about $5.21 per core a month), Datacenter at $0.041067, effective 1 August 2026 (checked 3 November 2026). Source: prices.azure.com
From request to a plan for every server
We send the inventory script within one business day of your request and deliver the plan within 3 business days of receiving its output.
- Day 1: Request the service; we confirm the server count and send the read-only inventory script.
- Day 2: You run the script on each server and send us the output.
- Day 3–5: We check each server and deliver the written plan and runbooks.
- Within 30 days: Follow-up questions answered; review call on the Small site plan.
Security and data
- The inventory script only reads configuration; it changes nothing, and you can read it before running it.
- We never ask for administrator passwords or remote access for the plan.
- Inventory output is stored encrypted and deleted 30 days after delivery, or earlier on request.
- Plans are shared only with the contacts you name.
Guides and answers
Windows Server 2016 end of life: 12 January 2027, dates and options
Windows Server 2016 end of life (end of support) is 12 January 2027 for all editions. ESU price per core, Essentials, upgrade paths and every version's dates.
Read the guide →Windows Server 2016 ESU cost: what Microsoft charges per core
Windows Server 2016 ESU cost through Azure Arc: about $5.21 per core a month (Standard) or $29.98 (Datacenter), 16-core minimum, back-billing and examples.
Read the guide →Questions
When does Windows Server 2016 support end?
On 12 January 2027, for all editions: Datacenter, Essentials, MultiPoint Premium and Standard. Microsoft says the January 2027 security update is the last one available.
Will my server stop working on 12 January 2027?
No. It keeps running, but it gets no more security updates, non-security updates or assisted support from Microsoft. Each new vulnerability found after that stays open.
Can I upgrade Windows Server 2016 straight to 2025?
Yes. Microsoft supports an in-place upgrade from 2016 to 2019, 2022 or 2025 using installation media, subject to restrictions such as no language change and no switch between Server Core and Desktop Experience. Each upgrade needs a licence for the new version.
Is there ESU for Windows Server 2016?
Yes, for Standard and Datacenter editions, from 12 January 2027 through January 2030, through Azure Arc for customers with Software Assurance, a server subscription or SPLA. Microsoft's price list has it at $0.007132 per core per hour for Standard and $0.041067 for Datacenter (checked 3 November 2026), with billing from 13 January 2027.
What happens to Windows Server 2016 Essentials?
Support ends on 12 January 2027, including for Essentials features such as Remote Web Access, and Microsoft says any Essentials capability that keeps working after that should be treated as unsupported. ESU is offered for Standard and Datacenter, not Essentials.
Do you carry out the upgrade?
Not in the plan price. The plan is written so that your team or any IT provider can carry it out; if you want us to help with the work, we quote it separately once the plan shows its size.
Is this an official Microsoft service?
No. Server 2016 Exit Plan is an independent IT service. We use Microsoft's published lifecycle, upgrade and licensing information, and your servers stay under your control.
Plan the exit while there is still a January to aim for
Send us the inventory, and within 3 business days you have a plan for every Windows Server 2016 machine. $199 per server, once.
Request service