Windows Server end of support
planned roles first.
We review your Windows Server estate against the end of support for Windows Server 2016, using an inventory you share, and give you a written plan: what to move first, how to move each role, what depends on what, and what to weigh before buying extended security updates.
Who it is for
Organisations that still run Windows Server 2016 or older, and need a sequenced plan rather than a list of servers. Microsoft’s lifecycle page lists the extended end date for Windows Server 2016 as January 2027.
What we review
- Inventory and versions. servers, operating system versions, roles, physical or virtual, owners and business impact. Our free server inventory analyzer helps you structure what you share.
- Lifecycle dates. each server mapped to its lifecycle date. Microsoft’s lifecycle page lists the extended end date for Windows Server 2016 as January 2027; check the current lifecycle page.
- Order of moves. a sequence based on which roles depend on which. Directory and name services are normally considered first because other roles rely on them.
- Domain controllers. Microsoft’s recommended way to upgrade is a clean install, promoting new servers and demoting older ones, rather than an in-place upgrade. The report checks FSMO role availability, which the promotion steps depend on (for example the schema master for forest preparation).
- Method for each server. in-place upgrade, clean install, migration or cluster rolling upgrade, which Microsoft lists with different trade-offs for downtime, hardware and role support. Not every role supports in-place upgrade, and the supported version gap is limited, so each role is checked against Microsoft’s role and feature migration matrix.
- DHCP, DNS, file and print. how each role is migrated, and what points at the old server: hard-coded names, drive mappings, printer connections and scripts.
- Remote Desktop Services and applications. which applications and Remote Desktop roles run on each server, and whether the application vendor supports the target Windows Server version.
- SQL Server and other databases. database version, application dependency and the order in which databases and their applications move together.
- Extended security updates versus migrating. Microsoft describes extended security updates as a last resort for products past end of support, and documents them for Windows Server 2012 and 2012 R2 as free in Azure and purchasable elsewhere. The report states what to check for your versions in current Microsoft documentation and sets out the inputs for comparing bridging with migrating, using our ESU comparison planner.
- Azure option. whether moving some servers to Azure virtual machines suits them. Azure Migrate helps assess Azure readiness and cost and plan the migration.
- Licensing, certificates and rollback. the licence position for the target version (Microsoft notes each Windows Server upgrade needs a separate licence), certificates and PKI that tie to old servers, and backup and rollback before every change, as Microsoft advises.
What you get
A written report, delivered through the channel agreed in the quote. It contains:
- An executive summary in plain language
- A server-by-server table: role, version, lifecycle date, suggested method and order
- A dependency map for identity, name services, file, print, applications and databases
- The inputs for an extended-security-updates versus migration comparison (no prices or savings are promised)
- A 30/60/90-day plan, and a list of what was not checked
See the format in the fictional report sample (sample, fictional data).
What we need from you
- A named contact with authority over the servers
- A server inventory (names may be pseudonymised), role list and application owners
- Any vendor support statements, licence summary and constraints such as change windows
How it works
- Send an enquiry. Tell us the question. Keep credentials and customer data out of it.
- Agree the written scope. We propose scope, fee and timing in writing. Nothing starts until both sides accept it.
- We review what you choose to share. We read only the inventory and documents in the agreed scope. We do not connect to your servers or run discovery tools.
- You get a written report. It says what was checked, what was not, and suggested next steps.
- Any change is approved separately. A report does not authorize changes; anything that changes needs its own written approval.
See what the report looks like: Read a fictional report sample (sample, fictional data). How we handle your information: Trust and data handling.
What we need from you. A named contact with authority, and a small set of evidence you choose to share through a channel we agree in writing first. Please do not send credentials, access tokens or customer exports through the enquiry form.
What we do not do. We do not connect to your servers, run discovery tools, upgrade or migrate anything, or buy or activate licences. We promise no costs, savings or dates.
What needs separate approval. Any upgrade, migration, cut-over or decommissioning, any purchase of extended security updates, and any follow-up check after changes.
Questions before an enquiry
When does Windows Server 2016 go out of support?
Microsoft’s lifecycle page lists the extended end date for Windows Server 2016 as January 2027. Check the current lifecycle page for the exact date and terms.
Should we buy extended security updates?
Microsoft describes them as a last resort for products past end of support. What is offered, and on what terms, depends on the version and changes over time, so check current Microsoft documentation. The report sets out the decision factors and the inputs for the comparison planner.
In-place upgrade or migration?
Microsoft lists in-place upgrade, clean install, migration and cluster rolling upgrade, with different trade-offs. For domain controllers Microsoft recommends promoting new servers and demoting old ones rather than upgrading in place. The report recommends a method per role.
Will you migrate the servers?
Not under this review. It produces the plan. Doing the migration needs its own scope, change approval and rollback plan.
Do you need access to our servers?
No. You share an inventory and documents through an agreed channel. We never receive credentials.
Free tools, reading and vendor documentation
- Server inventory analyzer (free)
- Certificate inventory analyzer (free)
- Windows Server 2016 migration planner (free)
- ESU, upgrade and migration comparison planner (free)
- Windows Server licensing calculator (free)
- Windows Server 2016 end-of-support guide
- Domain controller migration
- File server migration
- DHCP, DNS and NPS migration
- Print server migration
- RDS and RD Gateway upgrade
Microsoft documentation (opens in a new tab). Product behaviour and licensing change, so check current Microsoft documentation before acting:
Ready to start?
Tell us what you need. We reply to confirm fit and to propose scope, fee and timing in writing.