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Windows Server 2016 . support ends 12 Jan 2027

The deadline's fixed. Your bill isn't.

12 January 2027 is the same for everyone. What it costs you is not. Tap your answer and get your readiness score, your options and honest cost estimates in plain pounds.

Roughly how many of these older servers are you running?
That was question 1 of 6. About two minutes, no card, no obligation.
Skip the score, show me options & costs →
--days
--hrs
--min
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until it stops getting security updates
Microsoft Partner 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. Microsoft has confirmed Server 2016 ESU will be available for Azure workloads, and on earlier server versions Azure carried the ESU cost. 2016 pricing is not yet published, so Azure is the route most likely to soften the ESU bill while the trickier moves happen.

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 We run client environments to Cyber Essentials standards UK registered company Fixed prices, no per-server charging
If you want a plan, not just a score

Every server decided, on your terms

Not another score. A decision against each one, the real numbers behind it, and a plan you could hand to anyone.

  • You know which servers the business genuinely cannot lose, and which ones nobody would miss if they went tomorrow
  • Nothing is left in the "we will deal with that later" pile. Every server has a decision against it: keep, move, replace with a service, or scrap
  • You decide on money, not on a deadline. What staying put costs, what new hardware costs, what the cloud costs, and crucially what each one costs to run afterwards rather than just to move to
  • You do not get sold a like-for-like move you did not need. If there is a cleaner or cheaper way, an architect tells you, and the price does not change whichever way you go
  • You stop carrying it. Whoever asks, internally or externally, gets a straight answer and a date
  • You keep the plan whether we do the work, your own people do it, or nobody does
The Server Action Plan
Fixed fee, agreed before anything starts.
If it does not turn up either a risk you did not know about or avoidable cost worth more than the fee, you do not pay.
And if you go ahead with the work afterwards, the fee comes off it in full.
Find out if it is a big job or a small one
Start with half an hour, nothing to prepare. You come away knowing which servers are actually the problem and roughly what each route costs, whether or not the plan follows.

A full move runs three to six months when nothing surprises you. From about October, January stops being reachable and the conversation changes from moving to buying time.

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.