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.

 

Version jumps to get from Windows Server 2008 to 2019
Different potential ways to upgrade from Windows Server 2008 to Windows Server 2019

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”.

Part 1 - Check the version of your current operating system

Part 1 – Check the version of your current operating system

Once you have this information, it’s time to save your system configuration and network settings as a text file.

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).

Part 1- Compiling information about the current operating system and network settings

Part 1- Compiling information about the current operating system and network settings

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).

Part 2 - Launch the Windows Server 2012 R2 installer

Part 2 – Launch the Windows Server 2012 R2 installer

The program will then load an image for the installation and copy the necessary temporary files. This process can take a while depending on your server specifications (RAM, CPU, disk, etc.).

Part 2 - Wait for temporary files to be copied

Part 2 – Wait for temporary files to be copied

The installer will then show a window asking whether you want to get important updates.

In this window, you will also be asked whether you want to help make the Windows installation better (8). Personally, I like to tick these checkboxes as it allows Microsoft to gather data on systems, installations, errors, etc. and use them to make improvements.

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

Part 2 - Choose "Go online to install updates now"

Part 2 – Choose “Go online to install updates now”

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”.

Part 2 - Select the version of Windows 2012 R2 that you wish to install.

Part 2 – Select the version of Windows 2012 R2 that you wish to install.

The next window will show you the License Terms. Here, they have been heavily summarised, so there’s no excuse for not reading them. At last, you’ll be able to say that you actually read an EULA and dispel the myth that no one ever reads the license terms!

Accept the license terms by ticking the checkbox and click on “Next” (11).

Part 2 - Review and accept the licence terms for Windows Server 2012 R2

Part 2 – Review and accept the licence terms for Windows Server 2012 R2

The next window will ask you which type of installation you want, and there are only two options:

  • 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).

Part 2 - Choose the Upgrade option to install WS2012R2

Part 2 – Choose the Upgrade option to install WS2012R2

At this point, you will see a brief warning about the compatibility report, which is saved to your desktop.

The program will also recommend visiting the page titled “Install, Upgrade, or Migrate to Windows Server”, where you’ll find additional information about migration. Since we did a fair bit of preparation at the beginning of the tutorial, this step isn’t strictly necessary.

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

Part 2 - Read the warning about the compatibility of applications on WS2012R2

Part 2 – Read the warning about the compatibility of applications on WS2012R2

The upgrade process will now start and the window shows the five stages of the process:

  • 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 2 - Wait while the server upgrades to WD2012R2

Part 2 – Wait while the server upgrades to WD2012R2

After the system has restarted several times, you will finally see Windows Server 2012 R2 start screen. Log in to the OS and get ready to upgrade to WS2019.

At this point, it’s a good idea to check that there aren’t any issues, that everything has been configured correctly, that services run properly, etc. If everything is fine, you can rest assured that everything should work correctly in the next step.

Part 2 - The Windows Server 2012 R2 start screen

Part 2 – The Windows Server 2012 R2 start screen

Once you’re satisfied that everything is OK, it’s time to move on to the next stage: upgrading from Windows Server 2012 R2 to Windows Server 2019.

 

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.

Part 3 - Extract the configuration information on WS12R2 before upgrading

Part 3 – Extract the configuration information on WS12R2 before upgrading

Once you’ve done this, launch the Windows Server 2019 upgrade by browsing to the drive where you mapped the image and double-click on it (16).

Part 3 - Launch the Windows Server 2019 installer

Part 3 – Launch the Windows Server 2019 installer

The Windows Server 2019 installer is quite a bit different from Windows Server 2016. Firstly, it is much quicker. This is because the binaries are copied while still compressed, then decompressed on the target machine and then configured. The previous version copied a large number of small files which greatly slowed things down.

At this point, simply wait for the packages to be copied.

Part 3 - Wait while the installer starts

Part 3 – Wait while the installer starts

As with the previous upgrade, you’ll be asked whether you want to get updates, drivers and optional features. Once again, I prefer to choose the option “Download updates, drivers and optional features” (17). If you decide to opt for the second option, there will be no great impact on the upgrade. You’ll just have to spend time downloading updates afterwards.

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”.

Part 3 - Choose the option to download updates

Part 3 – Choose the option to download updates

Next, you need to choose the image to be deployed on the server, which should be consistent with your previous choice. For this tutorial, we’ll select “Windows Server 2019 Standard (Desktop Experience)” (19) 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!

Part 3 - Select the version of Windows Server 2019 that you wish to install

Part 3 – Select the version of Windows Server 2019 that you wish to install

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

Part 3 - Check the WS2019 license terms and click Accept

Part 3 – Check the WS2019 license terms and click Accept

The next step is a critical point in the process because you will be asked whether you wish to keep your personal files and apps (21). If you make a mistake and select the second option, you will lose everything because the system will be completely formatted. You will have to use a backup to restore everything you have lost and start the whole process again.

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

Part 3 - Select the option to keep existing files

Part 3 – Select the option to keep existing files

The program will now start downloading updates. Just sit patiently and wait for the process to finish.

Part 3 - Wait while the program downloads updates for WS2019

Part 3 – Wait while the program downloads updates for WS2019

Once all updates have been downloaded, you’re ready to install Windows Server 2019. The installer will show a window listing your installation choices.

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.

Part 3 - Review your chosen options before proceeding to install WS2019

Part 3 – Review your chosen options before proceeding to install WS2019

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.

Part 3 - Wait while WS2019 is installed on the server

Part 3 – Wait while WS2019 is installed on the server

Once the installation is complete, you will see the server login screen. Simply use your administrator login to sign in with the necessary privileges.

Part 3 - Finally, you can enjoy your new Windows Server 2019

Part 3 – Finally, you can enjoy your new Windows Server 2019

Now that the entire process is complete, all that’s left to do is check that everything works properly and there are no issues with any of your apps, roles or services.

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!

Categorias:Servers