Upgrading server infrastructure is one of the major project now days, especially with Microsoft ending support for older operating systems. If you're still running Windows Server 2012 R2, it's high time to consider upgrading to Windows Server 2016 or 2019. In this blog, i am going to perform in-place upgrade from windows server 2012 r2 to 2019, ensuring a smooth transition with minimal downtime.
The upgrade will perform on virtual machine hosted on VMware ESXi environment.
Why we should Upgrade to Windows Server 2019?
Before diving into the upgrade steps, let's first highlight why upgrading is essential:
- Security Enhancements: Windows Server 2019 offers advanced security features like Windows Defender ATP and Shielded Virtual Machines.
- Performance Improvements: Benefit from enhanced performance, scalability, and reliability.
- Support for Modern Applications: Ensuring better support for containers, hybrid cloud, and modern workloads.
- End of Support: Windows Server 2012 R2 reached its end of support in October 2023, meaning no more security updates or technical support.
Pre-Upgrade Checks
1. Check System Requirements
Ensure hardware meets or exceeds Windows Server 2019 requirements:
- Processor: 1.4 GHz 64-bit processor (2 GHz or faster recommended)
- RAM: Minimum 2 GB (ECC recommended) at least 4 GB require for smooth process
- Disk Space: At least 32 GB
- Network: Gigabit (10/100/1000baseT) Ethernet adapter
2. We need to check Application Compatibility.
Review all applications and roles running on your server.
Use the Microsoft Assessment and Planning Toolkit to identify potential issues if any.
It can be downloaded from Microsoft Download Center
3. Backup Your Server
In my case, i am performing this upgrade on virtual machine so we need to take non-memory snapshot/clone of the target vm as backup.
Note: If you have large vm size then detach non-OS drive first from VM to avoid large snapshot/clone image size, once upgrade gets successful, attach non-OS drives, make sure note down the path of datastore and VMDK disks.
Otherwise take a full system backup using Windows Server Backup or your preferred backup tool.
Backup all critical data, including databases, configuration files, and virtual machines.
4. Install Latest Updates
Ensure Windows Server 2012 R2 is fully patched with latest updates.
Drivers and firmware should be up to date.
5. Check License and Activation
Ensure you have a valid Windows Server 2019 license key. In my case i am using standard SOE so it doesn't prompt for license key.
Verify your current system’s activation status.
In-Place Upgrade having some dependency and Limitations.
- Direct Upgrade Path- We can upgrade directly from Windows Server 2012 R2 to Windows Server 2019, but not from earlier versions.
- Edition Matching- We can only upgrade to the same edition or higher (e.g., Standard to Standard, Datacenter to Datacenter).
- Roles and Features- Some roles may require reinstallation or reconfiguration post-upgrade.
Implementation steps
1. Insert the Windows Server 2019 Installation Media - we can use DVD, USB, or mount the ISO file and Run "setup.exe" (run as administrator) from the installation media or open mounted drive to run Setup.exe.
2. Start the Upgrade Wizard - On the Windows Setup screen, select “Download updates, drivers and optional features (recommended)” for the latest updates or select "Not right now" if you are planning to patch server after upgrade using patching tool. Click Next.
3. Enter Product Key - Enter your Windows Server 2019 product key when prompted. Click Next.
If you are using standard ISO this would not require , it can also activated after upgrade using GUI (Settings App), Command Prompt (slmgr.vbs), KMS (Key Management Service) or Phone Activation.
In my case product key is not require during upgrade.
4. Select Windows Server Edition - Choose the edition matching your current installation.
Ensure you select the same “Desktop Experience” or “Server Core” as your existing setup. Next.
5. Accept License Terms - Read and accept the license agreement. Click Next.
6. Choose Upgrade Option - Select Keep personal files and apps. This ensures an in-place upgrade. Click Next.
7. Compatibility Check -The setup will check for compatibility issues. Review any warnings and
resolve them. If all checks pass, click Next to proceed.
8. Begin Installation - Click Install. The system will go through several reboot cycles. Do not interrupt the process.
9. Post-Upgrade Checks - After the upgrade completes:
- Log in and verify all drives, data, services, applications, and roles.
- Install the latest Windows updates for Windows Server 2019.
- Reapply Group Policies if needed.
- Remove deprecated features and clean up old files.
Common Issues and Troubleshooting
- Driver Incompatibility- Update or replace any drivers that do not work post-upgrade.
- Application Issues- Some legacy applications may not function correctly. Consider running them in compatibility mode or upgrading them.
- Activation Problems- If Windows is not activated, re-enter your license key or contact Microsoft support.
Best Practices for a Smooth Upgrade
- Test in a Lab Environment- Always test the upgrade process in a non-production environment first.
- Schedule Downtime- Plan the upgrade during off-peak hours to minimize user impact.
- Document Everything- Keep a record of your current server configuration and the steps taken during the upgrade.
Conclusion
Upgrading from Windows Server 2012 r2 to Windows Server 2019 ensures infrastructure remains secure, supported, and ready for future workloads.
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