Windows Server 2019 EOL: What You Need to Know

Garrett Wiesenberg
March 4, 2025
Managed IT Services, Server Management

On January 9, 2024, Windows Server 2019 officially ended mainstream support. While Microsoft will continue to provide security updates until January 9, 2029, the operating system isn’t receiving new features or bug fixes.

What does that mean for you? Is it time to upgrade, or can you stick with Server 2019 while you focus on migrating from Windows 10 to Windows 11?

The answer depends on your unique situation, your business goals, and how you want to approach server support and hosting. Whether you’re working with a managed service provider or doing it all yourself, here’s everything you need to know.

Key points:

You don't need to migrate today if Windows Server 2019 is working for you.
You should prioritize Windows 11 upgrades before addressing Server 2019.
Cloud migration is another option for moving away from Server 2019.
An MSP (managed services provider) can help you find the right path if you're not sure.

What’s the support timeline for Windows Server 2019?

Mainstream support ended January 9, 2024. The operating system is no longer receiving feature updates, non-security related updates, or complimentary support from Microsoft.
Extended support will end January 9, 2029. Until this date, the operating system will continue to receive security updates and paid support.

Do we need to migrate off Windows Server 2019 in 2025?

Not necessarily.

Windows Server 2019 is still a secure operating system, since Microsoft is providing security updates until 2029. The OS won’t turn into a sitting duck for cyber-attacks any time soon.

But Windows Server 2019 won’t receive any new features from Microsoft. If you’re going to keep it for now, you’ll have to run it with its current capabilities as they are.

Microsoft also won’t provide bug support for free. You can get help with a bug, but you’ll have to pay Microsoft for the engagement. If the current feature set of Server 2019 is serving you well, and you don’t mind paying for the occasional support request, then there’s no need to migrate this year.

What’s the business impact of keeping Server 2019 for now?

You shouldn’t see any operational impact before 2029, other than an increased cost of support if you need to open any tickets with Microsoft.

That said, organizations should start planning their upgrade path. You want to be prepared for 2029—or for the time before 2029 when you need to migrate for other reasons. Newer operating systems may offer greater benefits through new features, enhancements, and ongoing development.

What options do we have to replace Server 2019?

At a high level, you have two choices: Upgrade your OS or migrate to the cloud. Here’s what each option looks like.

Upgrade your OS. Moving to Windows Server 2022 or 2025 will put you back into mainstream support so you can receive new features and free support from Microsoft. This is a smart move, especially if you need enhanced capabilities and want to stay ahead of the curve. Of course, you’ll have to make sure that the software installed on your server is compatible with your chosen OS. Here at Corsica Technologies, we can help you make this determination.
Migrate to the cloud. This is a more drastic option, but it may be the right choice for your organization. This is especially true if you want to leverage more SaaS applications across your operations, or if you want to offload maintenance responsibilities completely. Learn more here: 4 Principles of Smart Cloud Migration Strategies.

Ready to save 15% on Microsoft 365?

Get up to 15% off MSRP for M365. Most companies save $20k-$200k/year.

Get your discount now!

Where should we focus in terms of Windows upgrades?

For organizations that can live with Server 2019 for now, it’s actually more important to look at upgrading workstations from Windows 10 to Windows 11. Windows 10 will stop receiving security updates on October 14, 2025, which gives you a clear deadline for addressing this required upgrade. Our current advice to clients is to focus on Windows 11 first, then look at upgrading from Server 2019.

That said, if you’re unsure what to tackle first, don’t hesitate to get in touch. We can help you determine what’s most important for your organization and advise on a path forward.

The takeaway: Get the guidance you need with Windows operating systems

Here at Corsica Technologies, we help clients make these decisions every day. Your organization is unique, and there’s no one-size-fits-all answer. That’s why we consult on your business goals, your current challenges, your current technology landscape, and where you need to go. Our experts can help you determine the right path forward so all your devices and systems stay up to date. Contact us today to start building a smart technology roadmap for your company.

The Corsica Difference »

You Won’t Find Our Value Anywhere Else:

Achieve outcomes that matter »

Industries Served

Your Business, Your Vertical:

Insights and Resources

Guides + Education:

Tools and Templates: