Guide · Servers
Windows Server 2019 end of life: plan your replacement now.
Microsoft stops security updates for Windows Server 2019 on 9 January 2029, and for Windows Server 2016 sooner, on 12 January 2027. Replacing a server takes planning, budget and downtime, so the time to start is well before the deadline.
By the PC1 support team · Updated November 2026
The dates
When each version of Windows Server stops getting updates.
| Version | Security updates end | Status |
|---|---|---|
| Windows Server 2012 and 2012 R2 | 13 October 2026 (final paid extension) | Ended: no more updates |
| Windows Server 2016 | 12 January 2027 | Ends in weeks; paid Extended Security Updates available |
| Windows Server 2019 | 9 January 2029 | Mainstream support ended January 2024; no extension announced |
| Windows Server 2022 | 14 October 2031 | Supported |
| Windows Server 2025 | 14 November 2034 | Current version |
Dates from Microsoft’s product lifecycle. Since January 2024 Windows Server 2019 has received security fixes only, with no new features.
Why plan now
A server replacement is a project, not a quick upgrade.
- Line-of-business software has to be checked, and sometimes upgraded, for the new version.
- Servers bought for 2019 may be due for replacement anyway, so hardware and the operating system are often renewed together.
- Moving files and sign-in to Microsoft 365 can remove the need for a server altogether, but takes time to do well.
- Spreading the cost over the next budget year is easier than a rushed purchase in late 2028.
- Unsupported systems fail Cyber Essentials, so certification depends on getting it done in time.
See Cyber Essentials certification for what the scheme requires.
Still on 2016?
Windows Server 2016 ends on 12 January 2027.
If you still run Windows Server 2016, it stops getting free security updates in January 2027. Microsoft sells Extended Security Updates for up to three more years, but they are an annual cost and only buy time. Most businesses are better off moving straight to a current version or to Microsoft 365, and we can plan both together if you also run 2019.
Your options
Four ways to replace an ageing Windows Server.
| Option | What it means | Best for |
|---|---|---|
| Move to Microsoft 365 | Files to SharePoint and OneDrive, email to Exchange Online, sign-in to Entra ID | Servers that mainly hold files and email |
| Upgrade to Windows Server 2025 | The current version, usually on new hardware | Software that must run on a server on site |
| Move to the cloud | Run the server in Azure or another cloud | Applications you need to keep but not the hardware |
| Isolate it | Cut it off from the internet and the rest of the network as a stopgap | Old equipment that cannot be replaced yet |
How we help
A plan, a fixed price, and no gap in service.
We list what each server does and what depends on it, recommend the right replacement, and move files, applications and users across with as little disruption as possible. At Ledwood we replaced end-of-life servers and systems and put a 24/7 Security Operations Centre around 200+ devices.
Windows Server 2019 questions
What people ask before switching.
When is Windows Server 2019 end of life?
Will there be Extended Security Updates for Windows Server 2019?
When does Windows Server 2016 support end?
Can we upgrade Windows Server 2019 to 2025 in place?
What happens to a server after end of life?
Free server review
Find out what it would take to replace your servers.
Send us your current IT, security, phone and CCTV costs. Within two working days a senior engineer sends back a written comparison showing where you are overpaying and what we would change. No obligation, no sales script.
- Reply within one working day
- Fixed prices, in writing
- A senior engineer, not a salesperson