As tech keeps moving forward, keeping track of software lifecycles is key to staying secure and efficient. On January 9, 2024, Windows Server 2019 hit end of mainstream support, which means no more new features or non-security bug fixes. You’ll still get security patches until 2029, but if a bug shows up, you’re on your own. So, should you upgrade now or ride it out a bit longer. Either way, with Server 2019's timeline ticking, now’s the moment to plan ahead.
The Lifecycle of Windows Server 2019
The Windows Server 2019 lifecycle follows Microsoft’s Fixed Lifecycle Policy, which outlines exactly how long you can expect updates and support. This policy splits support into two main phases: mainstream support and extended support. Understanding these timelines helps IT admins and business owners know when to maintain, when to upgrade, and when to start planning for change. Here’s a breakdown of what each phase means for you.
Mainstream Support (Ended January 9, 2024)
Mainstream support for Windows Server 2019 ended on January 9, 2024. Until that date, Microsoft regularly provided feature updates, bug fixes, and design improvements. If something went wrong or a new tool was needed, you had a safety net. That safety net is now gone; no more feature development or non-security patches will be delivered from here on out.
Extended Support (Until January 9, 2029)
From now until January 9, 2029, Windows Server 2019 end of life looms on the horizon. This phase only includes security updates, which means critical patches will still roll out to protect your systems, but don’t expect enhancements or quality-of-life fixes. It’s a maintenance phase, not a growth phase. This is the final stretch of official support, so it’s a good time to begin preparing for what's next.
Three Upgrade Options for Windows Server 2019 End of Life
Now that Windows Server 2019 has exited mainstream support, it’s time to plan your next steps. While you can continue using it for a while, the absence of new features or bug fixes makes it wise to explore Windows Server 2019 upgrade options. Microsoft offers three paths tailored to different business needs: an in-place upgrade to Windows Server 2022, migration to Microsoft Azure, or a fresh installation of a newer version. Let’s break them down so you can make an informed decision.
Method 1: In-Place Upgrade to Windows Server 2022
Check System Requirements
Before anything else, you need to make sure your current hardware can run Windows Server 2022. Microsoft’s minimum specs are:
Processor: 1.4 GHz 64-bit processor (minimum)
RAM: 512 MB (2 GB for Server with Desktop Experience)
Storage: 32 GB minimum, but realistically, you’ll want at least 60 GB free
Firmware: UEFI and Secure Boot recommended
Here's how you can check for the requirements on your pc:
Step 1: Hover down to the bottom-left corner of your screen and click the Start button (yep, the one with the Windows logo).
Step 2: In the search bar, type “About your PC” and hit Enter.
Step 3: Under Device specifications, check your installed RAM, make sure it’s 512 mb or more.
Step 4: To check your storage, go back to the Start menu and type “Disk Management”.
Step 5: Look for your C: drive and make sure it has at least 32GB of free space.
Step 6: To check for your firmware, open up Device Manager. Press the “Windows key + X” on your keyboard, and from the menu that pops up, click on “Device Manager.”
Step 7: From there, find firmware and click on it, and then double-click system firmware. It should show a new window showing what your current firmware is.
Backup Your Current System
Before you start the upgrade, backup your system, seriously, don’t skip this. Even though in-place upgrades usually keep your files and settings, there’s always a risk that something could go wrong. I recommend using Windows Server Backup or a solid third-party tool. Make sure to cover the system volume (C:), important data directories, configuration files, and Active Directory if your server runs it. Once done, verify the backup. A broken restore is worse than none at all.
Upgrade process
Step 1: Once the ISO file is downloaded from the Microsoft Evaluation Center, right-click on it and select Mount. This opens the ISO as a virtual DVD drive (e.g., D:).
Step 2: If required, enter your Windows Server 2022 product key. If you're using the Evaluation ISO, this step may be skipped.
Step 3: Next, select which edition to run. Choose the same edition you're currently using, Standard or Datacenter, with or without Desktop Experience. Mismatching editions will block the upgrade.
Step 4: Review and accept the Microsoft license terms to continue.
Step 5: Select “Keep personal files and apps” to preserve your settings, roles, and installed features. Click Next.
Step 6: The installer will now run a compatibility check. Fix any issues it detects (unsupported roles, low storage, etc.) before moving forward.
If everything is ok. The upgrade process will start, and the system will reboot several times.
Method 2: Migration to Microsoft Azure
If you're planning for scalability, flexibility, and reduced on-prem maintenance, migrating from Windows Server 2019 to Azure could be your best long-term move. Microsoft Azure isn’t just cloud storage, it’s a full ecosystem for hosting, managing, and scaling your workloads securely and efficiently.
Before you begin migrating to Azure, it’s essential to assess your current environment using Azure Migrate. This tool helps you discover on-premises servers, evaluate their readiness, and estimate costs in Azure. Once the assessment is complete, plan your migration strategy, whether you’ll rehost (lift-and-shift), replatform, or refactor based on your business needs.
After planning, execute the migration using the appropriate Azure tools, such as Azure Migrate appliance, AzCopy, and VM image creation. Once your workloads are running in Azure, validate the migration by testing services, configurations, and performance. Finally, optimize your new environment with tools like Azure Monitor and Azure Advisor to ensure security, cost-efficiency, and long-term stability.
Method 3: Fresh Installation of a Newer Version
If you’re staying on-premises, a fresh install of Windows Server 2022 or 2025 is a clean, reliable way to upgrade. It ensures continued support, security, and performance improvements without relying on the cloud.
Step 1: Head over to the Microsoft Evaluation Center or your Volume Licensing Service Center and download the official ISO for Windows Server 2022. This ISO file is what you’ll use to create a bootable install medium.
Step 2: If you're installing on physical hardware, plug in a USB drive (8 GB or larger) and open Rufus. Under Device, select your USB.
Step 3: In the Boot selection field, browse and select the Windows Server 2022 ISO you downloaded. Keep the default settings and click Start. This will turn your USB into a bootable installer.
Step 4: Restart your server and enter the BIOS or UEFI settings by pressing the appropriate key (usually F2, Del, or F12) during startup.
Step 5: Change the boot order so that your USB drive (or ISO if using a VM) is first. Save and exit. Your machine should now boot into the Windows Server setup.
Step 6: When the installer loads, choose your language, time, and keyboard settings, then click Next.
Note: If prompted, enter your product key or choose “I don’t have a product key” to proceed with the evaluation version.
Step 7: On the new window that pops up, click “Install now”.
Step 8: On the next screen, choose the edition of Server 2022 that best fits your needs.
Step 9: Go ahead and pick the "Custom: Install Windows only (advanced)" option.This will ensure that you are going through a clean install.
Step 10: On the next screen, you’ll see your hard drives and partitions. Delete any old partitions if needed, then select the unallocated space and click Next.
Step 11: Windows will begin copying files and installing the OS. This step can take several minutes. Your system will restart several times, don’t interrupt the process.
Step 12: After the final reboot, you’ll be asked to set up an Administrator password. Enter a strong password and continue. You’ll then be taken to the login screen for your fresh Windows Server 2022 system.
Leverage WPS Office in Your Server Environment
Here’s something many sysadmins overlook: your office suite. And this is where WPS Office shines.
I’ve been using WPS for years, especially in lean server environments where resource optimization matters. It’s lightweight, compatible with Microsoft Office formats, and honestly, the cost-efficiency has saved my clients thousands.
Advantages of WPS Office:
Compatibility
WPS Office works seamlessly with .docx, .xlsx, and .pptx files, ensuring no formatting issues or conversion headaches. For example, I’ve shared complex .pptx presentations with teams using other software, and WPS preserved layouts and animations perfectly.
Resource-Friendly
On virtual machines with limited resources, WPS Office is impressively lightweight. I’ve run it on a 2 GB RAM VM alongside other critical apps without any slowdowns, a lifesaver for performance-conscious environments.
Cost-Effective
WPS Office’s free version packs powerful features like pivot tables and professional-grade presentation tools. For small teams, it’s a budget-friendly alternative to premium office suites, delivering exceptional value without compromise.
How to Install WPS
One of the standout features of WPS Office is its built-in AI support. I’ve used WPS AI for formatting, rewriting, and summarizing documents during server work, it saves a ton of time. Now, here’s how to download WPS Office:
Step 1: Begin by heading over to the official website of WPS Office.
Step 2: Click on “Free Download”, then once it’s finished, just open up the setup file to get started.
Step 3: After you click on 'Free Download', you’ll get the installer file. Just go ahead and click on that file to open it up.
Step 4: A window will pop up after you click on the installer file, asking you to agree to the terms and conditions. Take a quick look at them, and if you’re good to go, click on “Install Now” to start the installation process.
Step 5: The installation will begin right away! Just sit back and let it finish. Once it's done, you'll be all set to start using the program.
FAQs
Q1: What happens after Windows Server 2019's extended support ends?
After January 9, 2029, Windows Server 2019 will no longer receive security updates or support, increasing exposure to security risks.
Q2: Can I continue using Windows Server 2019 after its end of life?
Continuing to use Windows Server 2019 post end-of-life is technically possible but not advisable due to the absence of security updates.
Q3: Is WPS Office compatible with Windows Server operating systems?
Yes, WPS Office works seamlessly with Windows Server systems, providing a dependable office suite solution.
Closing Gaps Before Windows Server 2019 Ends
Whether you’re planning an in-place upgrade, migrating to Azure, or doing a clean install, the time to prepare is now, especially with Windows Server 2019 end of life drawing near. I’ve seen firsthand how proactive upgrades reduce downtime and prevent last-minute panic. And while you're modernizing your infrastructure, don’t overlook the smaller optimizations, like switching to WPS Office. Its built-in AI and smooth compatibility have been game-changers in nearly every deployment I’ve worked on.
