Upgrade Windows Server 2012 R2 to 2019: A Comprehensive Guide for Dev

Greetings, Dev! If you’re reading this article, chances are, you’re planning on upgrading your Windows Server 2012 R2 to the latest version, Windows Server 2019. Upgrading your server can be a daunting task, especially if you haven’t done it before. But don’t worry, we’ve got you covered! In this guide, we’ll walk you through the entire process, step by step, and help you make the transition smoothly. So, let’s get started!

Why Upgrade to Windows Server 2019?

Before we dive into the upgrade process, let’s first discuss why you should consider upgrading to Windows Server 2019. There are several compelling reasons to do so:

Improved Security

Windows Server 2019 comes with a host of security features that can help protect your server and data from cyber threats. These include Windows Defender ATP, Shielded VMs, and improved auditing capabilities. Upgrading can help you stay ahead of the ever-evolving threat landscape.

Better Performance

Windows Server 2019 has several performance enhancements that can help your server run faster and more efficiently. These include improved networking performance, faster storage, and better Hyper-V performance. Upgrading can help you get the most out of your server hardware.

New Features and Functionality

Windows Server 2019 has several new features and functionality that can help you take advantage of the latest technologies. These include support for Kubernetes, improved support for Linux containers, and a new Storage Migration Service. Upgrading can help you stay current and competitive.

Pre-Upgrade Preparation

Before you start the upgrade process, there are several things you need to do to prepare your server. These include:

Backing Up Your Data

Before you make any changes to your server, it’s always a good idea to back up your data. This will ensure that you have a copy of your important files in case something goes wrong during the upgrade process. You can use Windows Server Backup or any other backup solution of your choice.

Checking System Requirements

Before you upgrade to Windows Server 2019, you need to make sure your server meets the system requirements. These include:

System Requirements
1.4 GHz 64-bit processor
2 GHz or faster multi-core processor
512 MB
4 GB or more
Storage Space
32 GB
64 GB or more
Network Adapter
1 Gbps
10 Gbps or more

Make sure your server meets these requirements before proceeding with the upgrade.

Checking Application Compatibility

Before you upgrade to Windows Server 2019, you need to make sure your applications are compatible with the new operating system. Check with your software vendors to ensure that their applications are supported on Windows Server 2019. If you’re using custom applications, test them in a non-production environment before upgrading.

Checking Driver Compatibility

Make sure all your hardware drivers are compatible with Windows Server 2019. Check with your hardware vendors to ensure that they have drivers available for the new operating system. Installing incompatible drivers can cause system instability and other issues.

Upgrade Process

Once you’ve completed the pre-upgrade preparation, you’re ready to start the upgrade process. Here’s how:

Step 1: Download Windows Server 2019

The first step is to download the Windows Server 2019 ISO file from the Microsoft website. You can download the evaluation version or purchase a license if you’re ready to upgrade. Make sure you download the correct version based on your server’s architecture (x86 or x64).

Step 2: Mount the ISO File

After downloading the ISO file, you need to mount it on your server. You can do this by right-clicking on the file and selecting “Mount” or by using a third-party tool like Daemon Tools or WinCDEmu.

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Step 3: Run the Setup Program

Once the ISO file is mounted, navigate to the root folder and run the setup.exe file. This will launch the Windows Server 2019 setup program. Follow the on-screen instructions to start the upgrade process.

Step 4: Select Upgrade Option

When prompted, select the “Upgrade” option to perform an in-place upgrade. This will preserve your existing applications, data, and settings. Alternatively, you can perform a clean install if you prefer to start from scratch.

Step 5: Follow On-Screen Instructions

Follow the on-screen instructions to complete the upgrade process. The setup program will copy files, install updates, and reboot your server several times. Make sure you don’t interrupt the process or turn off your server during this time.

Step 6: Verify Upgrade

Once the upgrade process is complete, verify that your server is running Windows Server 2019. You can do this by checking the version number in the System Properties dialog box or by running the “winver” command in the Command Prompt.

Frequently Asked Questions (FAQ)

1. Can I upgrade from Windows Server 2012 to Windows Server 2019 directly?

No, you cannot upgrade directly from Windows Server 2012 to Windows Server 2019. You must first upgrade to Windows Server 2016 and then to Windows Server 2019.

2. What happens to my applications and data during the upgrade process?

If you choose the “Upgrade” option during the setup process, your applications, data, and settings will be preserved. However, it’s always a good idea to back up your data before upgrading, just in case.

3. How long does the upgrade process take?

The upgrade process can take several hours, depending on the size of your server and the speed of your hardware. Make sure you have enough time set aside for the upgrade and don’t interrupt the process once it’s started.

4. What if I encounter issues during the upgrade process?

If you encounter any issues during the upgrade process, such as error messages or system crashes, make sure you have a backup of your data and try the process again. If the issues persist, you may need to seek help from a professional.

5. Do I need to upgrade all my servers at once?

No, you can upgrade your servers one at a time if you prefer. However, make sure you plan the upgrade process carefully to avoid any compatibility issues between different versions of Windows Server.


Upgrading your server can be a complex process, but with the right preparation and guidance, you can make the transition smoothly. We hope this guide has helped you understand the steps involved in upgrading from Windows Server 2012 R2 to Windows Server 2019. If you have any questions or comments, feel free to leave them below. Happy upgrading!