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Windows Server 2016 . support ends 12 Jan 2027

Your Server 2016 has a deadline. See what it means for you, and what it costs.

Two quick ways to find out where you stand: a 2-minute readiness score for your exact setup, or cut straight to your options and their real costs in plain pounds.

Get my readiness score → Cut to the chase: options & costs →
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until it stops getting security updates
Microsoft Partner Cyber Essentials Certified 20+ years, plain English Fixed price, no lock-in
The three ways through

You have real choices while there is still runway

A migration done with months of runway has a very different risk profile to one done in a panic in December. Here is what the options actually look like.

Cleanest path

Upgrade to a modern server

Like-for-like onto Windows Server 2025, supported into the 2030s. The obvious move if the hardware is sound and the workloads are happy where they are.

Aging hardware

Move to Azure

If the box is as tired as the software, Azure is worth a look. Server 2016 workloads in Azure get Extended Security Updates at no extra cost, which buys breathing room for the trickier moves without the per-box bill.

Burned before

Phased cutover

For anyone who has had a migration go sideways: low-risk servers move first to prove the process, then the business-critical cutover happens to a rehearsed plan, not a hope.

Who is behind this

The straight version, from the person you would actually deal with

Eric, HiltDigital
"Most owners don't want a lecture about their servers. They want someone to look properly and tell them straight: keep this one, move that one, scrap the one nobody has touched in years. That is all this is. I have spent twenty-plus years doing exactly that for places with a lot more than a deadline on the line, so yours is very doable if we start now. No jargon, no quote padded with kit you do not need."
Eric, HiltDigitalI will be the one you actually talk to . 20+ years sorting this out
Microsoft Partner Cyber Essentials certified (we hold the cert we help you pass) UK registered company Fixed prices, no per-server charging
If you want a plan, not just a score

Server Action Plan

  • A proper sit-down to understand your business and what each server actually does for you
  • A full list of every server you have got, with the ones the business cannot lose clearly flagged
  • A straight call on each one: keep it, move it to the cloud, or scrap it
  • The plain maths on paying to stay put versus upgrading versus the cloud, decided on cost and fit, not on a deadline
  • A clear, step-by-step plan you keep, whoever ends up doing the work
Every server decided,
on your terms
The position to be in: keep, move or scrap, each one called on cost and fit, with the deadline irrelevant because you moved first. Most businesses get there in weeks, not months.
Book a 15-min call
Start with the call. The review only follows if it is genuinely worth it for you.
Straight answers

The questions we get asked first

You can, as a bridge. But ESU covers critical and important security patches only, the price climbs every year, and it is capped at three years before ending entirely in January 2030. It also does nothing for your other software: once Microsoft ends support, your vendors quietly stop testing against that OS, so you can pay for ESU and still find your backup tool throwing errors months later. For one specific blocker with a firm date, ESU makes sense. For everyone else it is an escalating bill for a problem you still have to solve.
Insurers have been tightening the "supported software" wording in cyber policies for a while. Running an end-of-life server past the deadline can sit on the wrong side of that clause, which means a claim in 2027 could come back as a declined payout rather than a settlement. The server does not even have to be the way in for the claim to be questioned. It is worth a quick word with your broker, and we are happy to answer whatever they raise.
Yes, if you start now. A straightforward estate can move comfortably inside the runway. A complex one needs the time, which is exactly why starting the conversation now gives you options that a December scramble does not. The scorecard tells you honestly which camp you are in.
Because you are paying for the thinking, not the boxes. Per-server is the commodity frame. The fixed fee is for an architect to understand your business, your workloads and what should move where, and to hand you a roadmap you own. If migration delivery follows, it is scoped openly from the review, never assumed.