Hands-on · service 10

Windows Server 2016 support ends on 12/01/2027.

After that date the server gets no more security updates, unless you pay for an extension (ESU). Every newly found security hole stays open. There is enough time to do the move properly, but not to put it off.

Four ways forward

The right one depends on what runs on the server. That’s why we start with an inventory, not a hardware quote.

Option 01

A new server

When applications must run on your premises, such as an older accounting or production system. A new physical or virtual server on the current Windows Server 2025, with backups and documentation.

Option 02

To the cloud

Files to SharePoint and OneDrive, applications to their cloud version or to Azure. No server of your own in the office.

Option 03

A mix

What can go to the cloud goes to the cloud. What must stay on site runs on a smaller server.

A stopgap

Paid extension (ESU)

Microsoft offers Extended Security Updates for Windows Server 2016 for up to three years. They run through Azure Arc, are billed monthly from 13/01/2027, and need active Software Assurance, an SPLA licence or a Windows Server subscription. Useful if you can’t finish the move in time, but they modernise nothing. We check whether you qualify during the inventory.

Sources: Microsoft Learn, end of support in 2027; Microsoft Learn, Extended Security Updates through Azure Arc; Windows Server Blog, 25/02/2026.

How we go about it

  1. Inventory

    What runs on the server: applications, shared folders, printers, accounts and licences.

  2. Options and costs

    Cloud, a new server, or a mix, with three-year costs. We recommend one and say why.

  3. Plan

    We agree the details with your application vendors and plan the move outside working hours.

  4. Move and check

    Backups first, then the move, usually over a weekend. Then we check everything works and hand over the documentation.

Already out of support

Support for these products has already ended; only Windows Server 2016 is still to come, on 12/01/2027. If you still run any of them, include them in the same plan.

Source: Microsoft Learn, end-of-support lists for 2025, 2026 and 2027.

ProductEnd of support
Windows 1014/10/2025
Office 2016 and Office 201914/10/2025
Exchange Server 2016 and 201914/10/2025
Office 202113/10/2026
Windows Server 201612/01/2027

A typical situation

This is a typical situation, not a specific engagement. We describe what we would do and what you get.

Engineering consultancy · around 25 staff

The server nobody dares to touch

Everything runs on one Windows Server 2016 machine whose support ends on 12/01/2027. Nobody knows exactly what’s on it.

What we do

  • Inventory the server, applications and licences
  • Options: cloud, new server, or a mix, with three-year costs
  • Backups first, then the move over a weekend

What you get

A supported platform, backups you can restore from, and documentation that belongs to you.

Questions

What happens on 13/01/2027?

The server keeps running as before. It just stops receiving security fixes, so every newly found security hole stays open. The risk grows every month.

Can we simply extend support?

Yes. Microsoft offers paid Extended Security Updates (ESU) for up to three years. The server must be connected to Azure Arc, and you need active Software Assurance, an SPLA licence or a Windows Server subscription. We check whether you qualify during the inventory. It’s a good stopgap if you can’t finish the move in time, but in three years you will face the same question.

Do we have to move to the cloud?

No. The cloud often makes sense, but not always, and some applications must run on site. We recommend what fits your applications and their three-year costs, not what’s fashionable.

Will there be downtime?

We plan the move outside working hours, usually over a weekend, and back everything up first. A short interruption at the moment of switching can’t be ruled out entirely, but we agree it with you in advance.

Will you buy the server and licences for us?

No. We choose the hardware and licences with you, and you buy them directly from whoever you like. We earn nothing on them, so we have no reason to recommend a pricier option.

How much does it cost?

The inventory costs from 9,000 Kč and is short. After it you get a fixed price for the whole move. We are not VAT-registered, so these prices are final.

Updated 13/10/2026

Let’s get it done calmly.

The first call is free and commits you to nothing. Within a few days you get a short proposal with a fixed price.