How to Upgrade from Windows Server 2008 to Windows Server 2019

In this tutorial, we’ll explain clearly how you can upgrade your server from Windows Server 2008 to Windows Server 2019.

Extended support for Windows Server 2008 and Windows Server 2008 R2 ended in January 2020. As a result, it is now very important to remove any servers that you might have that are running these operating systems.

The fact that they no longer receive support means they will no longer receive continuous updates for services, roles, etc. This includes security updates, so clearly the risks will only increase as online threats continue to grow.

All this means it’s vital that you upgrade your server to a more recent operating system, or at least one whose “end of life” or “end of support” date is as far away as possible.

At Jotelulu, we recommend jumping straight to the penultimate version of Windows Server, Windows Server 2019. Whilst this might sound odd, it is actually very common for IT technicians to opt for the penultimate version to guarantee a certain level of stability. While the most recent version of an operating system might have some great features, the previous version is more likely to have had any problems identified and addressed and the system is likely to be more stable.

Windows Server 2019 also has a good life ahead of it yet. It will receive initial support until 2025 and extended support until 2029 and it’s possible that this might also be extended. So, you can be sure of at least 7 years of service with continuous updates, security patches, etc.

The problem is that it isn’t actually possible to jump straight from Windows Server 2008 to Windows Server 2019. First, you’ll need to upgrade to an intermediate version and then jump to the 2019 edition.

If you’re starting from Windows Server 2008, you can upgrade to Windows Server 2012, then Windows Server 2016 and then finally to Windows Server 2019.

On the other hand, if you’re starting from Windows Server 2008 R2, you can upgrade to Windows Server 2012 R2 and then straight to Windows Server 2019.

Below you’ll see an illustration of the different options based on documentation from Microsoft.

NOTE: Before we move on to the next section, I’m just going to take the opportunity to say that we recommend, wherever possible, migrating to a new server instead of upgrading your existing server. This way, you should avoid any potential compatibility issues and avoid any loss of service as we’ll perform all the necessary tests beforehand. Furthermore, you’ll only turn the old server off once the new server has been put into production. This method will also mean that the upgrade process won’t leave any residual files or other junk in your file system.

How to Upgrade from Windows Server 2008 to Windows Server 2019

Before you begin

To successfully complete this tutorial and upgrade your server from Windows Server 2008 to Windows Server 2019, you will need:

• A server running Windows Server 2008 or Windows Server 2008 R2.
• A licence for the operating systems being used.
• CD/DVD images for the versions you wish to install.
• Backups of the server that you are going to upgrade in case there are any issues.

Part 1 – Preparing the Upgrade

Although the installation process is actually quite simple, like any IT task, it’s definitely worth spending a bit of time doing some prior planning if you want to avoid any potential problems later.

First, it’s a good idea to check whether you’re likely to have any compatibility issues with the applications and services that you use. You can do this by checking the manufacturer’s documentation, but we always recommend running a pilot test on a development or pre-production server to be sure.

You’ll also need to review the specification requirements for your new operating system to check that your hardware has enough CPU, RAM and disk space to run your new system.

Next, you should make sure you have some recent backup copies. In fact, I would have at least two – one from a few days ago and another made just before you perform the upgrade. After all, prevention is better than cure.

Lastly, you should extract your current system information, including the current version, network settings, etc. All of this will be very useful if something goes wrong and you need to re-configure your system.

In any case, knowing which current version you have will tell you which upgrades you need to perform.

There are various ways to find out your current system information, but I prefer to use the command prompt by running the “systeminfo” command (1).

As you can see in the screenshot below, this command returns the OS Name” (2), which in this example is “Windows Server 2008 R2 Standard”.

In this part of the tutorial, we’re going to use the command prompt. Then, in the next part, we’ll use PowerShell so that you can see how both processes work.

To compile all your configuration information, run the following commands (3):

mkdir c:\info

systeminfo > c:\info\systeminfo.txt

ipconfig /all > c:\info\ipconfig.txt

Once you’ve done this, browse to the C:\info folder (4) to check the files have been created successfully. Then, open them to check the content of the files (5).

I also personally recommend keeping a copy of this information on another server in order to have an external copy.

Part 2 – Upgrading from Windows Server 2008 R2 to Windows Server 2012 R2

We are now ready to begin the process to upgrade from Windows Server 2008 R2 to Windows Server 2012 R2.

First, you will need to mount the image for the installer or insert your CD/DVD, whichever you are using. Click on the image to launch the installer manually (6) and click on “Install Now” (7).

Next, we recommend clicking on “Go online to install updates now (recommended)” (9).

If you have chosen to install updates, the program will now connect to the Microsoft network and download any available updates. If you did not choose this option, the program will move on to the next stage of the installation process.

NOTE: If you choose to install updates, you might find that the system fails to connect and ends up skipping this step. Don’t worry, you will still be able to apply updates later on.

The next window will ask you to select the operating system you wish to install, which for this example will be “Windows Server 2012 R2 Standard (Server with a GUI)” (10).

In this tutorial, we have chosen this operating system because we are starting with Windows Server 2008 R2 Standard. However, if you are starting from the Datacenter version, you should select Datacenter Edition.

Another important point to bear in mind is that Windows Server 2012 also offers an option called “Server Core”, which does not have a graphic user interface. This is designed for people who want to work using the command line. Be careful not to choose this version by mistake as it will be much more complicated to use. However, there is a solution should you choose this version by accident.

Once you have done this, click on “Next”.

• Upgrade: Install Windows and keep files, settings and applications.
• Custom: Install Windows only (Advanced).

Since we’re upgrading Windows Server 2008 to Windows Server 2012 R2, you should choose “Upgrade: Install Windows and keep files, settings and applications” (12).

Simply click on “Next” (13) to continue with the installation.

• Copying Windows files.
• Collecting files, settings and applications
• Getting files ready for installation.
• Installing features and updates.
• Almost done moving files, settings and applications.

It might seem an odd way to describe the process, but Microsoft can be like that sometimes.

As it moves through these steps, the system will restart several times. You should not do anything during this time. Simply leave it to run without interrupting it or loading the CD/DVD drive. Otherwise, the installation will start again from the beginning.

Part 3 – Upgrading from Windows Server 2012 R2 to Windows Server 2019

NOTE: Don’t forget to change the map the image for Windows Server 2019.

Just like the beginning of the previous stage, it’s a good idea to save your system configuration before you do anything. While you can probably skip this step in principle, it’s still a good habit to get into.

In this section, we are going to do everything using PowerShell to give you an example of how to do this. Once you’ve loaded PowerShell, simply type in the following commands (15):

Set-Location c:\info

Get-ChilItem

systeminfo > c:\info\systeminfo.txt

ipconfig /all > c:\info\ipconfig.txt

get-Content .\ipconfig.txt

Here is a quick explanation of what these commands do:

• “Set-Location” is the same as the “cd” command in CMD and changes the working directory.
• “Get-ChildItem” is the same as the “dir” command in CMD and makes a list of the directory.
• “Get-Content” is the same as the “cat” command in CMD and shows the contents of a file.

You’ll also be asked again whether you want to help make the installation of Windows better. We’re quite fond of helping, as this could have an impact on the user experience for future versions. So, we’ll mark the checkbox “I want to help make the installation of Windows better” (18) and click on “Next”.

Careful! Remember that there is a version called “Server Core” which does not have a graphic user interface and is operated using command line. It is the default option, so don’t get caught out!

At this point, you will be presented with the Applicable notices and license terms. Simply click “Accept” (20) to continue.

Select the first option, and click on “Next”.

Here, there are just two things to check (22):

• The version of Windows that you wish to upgrade to: Remember that there are two versions, Standard and Datacenter, and that each one is available as a Desktop Experience or as Server Core.
• Keep personal files and apps: Whether you wish to keep any of the files currently on the system. Since this is an upgrade, this is very important.

Once you’re satisfied that your choices are correct, click on “Install” (23). If you’ve made a mistake, click on “Back” to make the necessary changes.

The system will now begin installing WS2019 and the screen will show you the installation progress. There are various different screens shown during this process, but we won’t go into them in this tutorial for the sake of brevity.

The system will also restart several times. If you want to keep track of all the changes and restarts, it might be a good idea to connect to the server console, but personally, we recommend that you take the opportunity to sit down with a nice, hot cup of coffee and wait.

It might also be a good idea to search for any updates and check the firewall and security settings.

Conclusion

Windows Server 2008 and Windows Server 2008 R2 stopped receiving extended support in January 2020. That means it’s time to start retiring all these machines.

In this article, we’ve explained how to upgrade from Windows Server 2008 to Windows Server 2012 (or Windows Server 2008 R2 to Windows Server 2012 R2) and then to Windows Server 2019. We’ve also included plenty of recommendations and things to watch out for.

As you can see, the process is actually pretty straightforward, as long as you follow instructions correctly.

Thanks for choosing Jotelulu!