Windows Server 2008 Migration and Upgrade Guide

Microsoft is ending support for Windows Server 2008 soon. Learn how you can migrate or upgrade your server before it's too late to make the move!

As you might be aware, the extended support for Windows Server 2008 and 2008R2 will come to an end on January 14th, 2020. End of support means the end of regular security upgrades, and this can be very detrimental, bearing in mind a cyber-attack on your server can make you lose a lot of vital data and resources for your organization.

The 2008 family of products was great for its time, but it is recommended you now upgrade to the more current versions for better performance and improved security and updates. 

The end of support for 2008 products, including SQL Server 2008 and 2008 R2, which end n 9th July 2019, presents you an ideal chance to transform your IT platform and move your infrastructure and applications to the cloud, especially with the cloud-ready Microsoft current server products.

Microsoft announced to address this need. There will be an extended security update that will be available for Free in Azure in 2008 and 2008 R2 versions of Windows Server and SQL Server. 

As with any end-of-life scenario, you need to start thinking about how to either upgrade or perform data migration to newer supported versions and platforms.

You can use this period to migrate your workloads to Azure with no application code changes and with near-zero downtime. Doing so will give you more time to plan your path and your ideal server needs. 

Upgrading or Migrating; Which one to Choose?

There is a lot of assessments and planning that are involved with planning into performing data migration from one platform to another. This is particularly true if you have business-critical workloads that are running on platforms that are being deprecated. 

Most times, it can get confusing trying to figure out between migrating and upgrading and making a choice on which one is best for you. So, what is upgrading as compared to data migration? What is the difference between the two?

Upgrading Deprecating Microsoft Servers

When we talk about upgrading, in relation to Microsoft Server products, we are referring to an in-place upgrade. This means we are performing an upgrade of the Windows Server operating system that currently allows for an upgrade to a newer Windows Server operating system.

By default, the applications, roles, services, and other data that may be hosted on the server are brought forward during the in-place upgrade. 

Microsoft has published supported paths to accomplish the upgrade of Windows Server operating systems. In a nutshell, you mount the media, either physical or ISO file to a virtual or physical machine, and run the setup.exe file that is found on the Windows media. 

Most newer Windows Server operating system media will autorun and recognize that you are currently having a Windows Server operating system that is loaded, and will ask you if you want to perform an upgrade.

Upgrading Windows Server presents an easy way to keep all the same configuration and other roles that are installed on an existing server to a newer version of the Windows Server operating system. Note that the data migration process is part of the upgrade itself. 

Windows server 2008 migration

See the image below for running an in-place upgrade for Windows Server 2019

How to upgrade to windows server 2019

Though upgrading an existing server can seem to be the easiest way to get off a deprecating platform to a supported one, caution must be exercised. It is essential to verify compatibility and requirements before attempting any upgrade.

Migrating Deprecating Microsoft Server

With migration, the end goal is the same – get to a supported version of the Windows Server operating system. However, getting it is a bit different as compared to upgrading. 

Rather than mounting the install media for a newer Windows Server operating system, migration, data, services, and roles are moved to a newer server that has already been provisioned. 


Think of Windows 2008/R2 server that is serving multiple roles such as DHCP server, hosting custom applications, and file server.

When performing a migration, you could potentially migrate the roles and services to different newer servers instead of one. Through doing so, may not necessarily be required, you get the opportunity to split out roles and services during the migration process. 

So this brings us to another exciting topic; the pros and cons of both upgrading and migrating Microsoft servers. Let’s have a look.



  • The process is generally straightforward –you only need to mount a media and perform the upgrade
  • It will involve some downtime to perform the procedure for only the services and roles hosted by the server.
  • It allows keeping configurations and custom settings intact, which may be a bit difficult to replicate on a newer server.


  • With Windows Server 2008, it requires multiple stages to get to the latest Windows Server operating system.
  • There is downtime for all services and roles hosted by the server



  • Allows you to move roles and services one at a time
  • Allows you to rethink which roles and services are housed on which servers
  • It allows you to go directly to a newer Windows Server operating system since you are moving roles, services, and data only.
  • There is potentially less downtime.


  • It may be challenging to reproduce custom configurations since they will have to be reproduced on the destination server.
  • May require more testing to get customizations on the newer server right.

Microsoft Server 2008 Upgrade Paths and Strategies

When looking forward to performing an upgrade of Windows Server 2008/R2 to a new Windows Server platform, there are different considerations to be made. These include;

  • In an upgrade, the best option or maybe a migration instead?
  • Which Windows Server operating system is your target? - this will affect the upgrade path.
  • Are you going to remain on-premises, or will you re-host in the Azure cloud?
  • In case you want to re-host to Azure, should you consider replicating 2008 there first, then upgrade?
  • In the case of Windows Server 2008, are you currently using the 32-bit version?
  • Are you currently using Windows Server 2008 Core Edition?
  • Are you currently running the latest service packs for Windows Server 2008/R2?

Upgrading will follow a specific path. First, you will need to upgrade Windows Server 2008 or Windows Server 2008 R2 to newer platforms, Windows Server 2012 R2, and then from Windows Server 2012 R2 to Windows Server 2016. If your ultimate platform is Windows Server 2019, you will need to make another upgrade, from Windows Server 2016 to Windows Server 2019.

Keep in mind that each upgrade means setting you back on some downtime.

See the image below on upgrade paths.

Moving to azure cloud platform

Moving to Azure Cloud Platform

If you currently have Windows Server 2008/R2, you can upgrade on-premises or to Azure. This means IT admins yet have more options and possibilities when rethinking about upgrades. 

Today, the power of the cloud has become the driving force behind IT operations. The Microsoft Azure public cloud is an exciting platform to get things done. The Azure public cloud provides a reliable platform with many benefits for today’s businesses. 

Microsoft makes it very easy to get your virtual machines, including Windows Server 2008/R2 re-hosted in the Azure cloud. You will accomplish this using the Azure Site Recovery tool, a tool you can replicate your virtual machines to the Azure IaaS cloud, and then perform a failover to the new re-hosted copy of your virtual machines in Azure – sounds geeky? Ask your IT admin!

You can migrate your on-premises Windows Server 2008/R2 to Azure, and this will enable you to continue running them on virtual machines. With Azure, you will stay compliant, more secure, and add cloud innovation to your work. 

Here are some of the benefits you will get by migrating to Azure;

  • Security updates in Azure
  • You will get three more years of Windows Server 2008/R2 and essential security updates at no additional charge.
  • There are no charges in upgrading to Azure
  • You will adopt more cloud services when you are ready
  • You will leverage existing SQL Server and Windows Server licenses for cloud savings that are unique to Azure.

Upgrading Windows Server 2008 R2 to Windows Server 2012 R2

Apart from deploying your servers to the Azure cloud platform, a second secure way to perform server upgrades is to upgrade to Windows Server 2012 R2 platform. In case you want to keep the same hardware and all the server roles, you will need to do an in-place upgrade, as we have discussed earlier in this guide.

An in-place upgrade will allow you to go from an older operating system to a new one, while at the same time keeping your settings, server roles, and data intact. 

Before you can start your Windows Server upgrade, it is recommended that you collect some information from your devices, to help you with diagnosis and troubleshooting issues. This information will come in handy in case your upgrade fails, so ensure you store the information in a secure place where you can access it for future references.

To collect your info

  1. Open a command prompt, go to c:\windows\system32, and then type systeminfo.exe
  2. Copy, paste, and store the resulting system information in a secure place of your device
  3. Type ipconfig /all into the command prompt, and then copy and paste the resulting configuration information into the same location as above.
  4. Open the Registry Editor, go to the HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\WindowsNT\CurrentVersion hive, and then copy and paste the Windows Server BuildLabEx (version) and EditionID (edition) into the same location as above.

After you have collected all your Windows Server-related information, it is highly recommended that you perform a backup of your operating system, virtual machines, and apps.

Additionally, you must Shut downQuick migrate, or Live to migrate any virtual machines currently running on the server. You will not have any virtual machines running during the in-place upgrade. This is what we call downtime.

To perform the upgrade

  1. Ensure the BuildLabEx value says you’re running Windows Server 2008 R2
  2. Locate the Windows Server 2012 R2 Setup media, and then select setup-exe
Windows R2 Setup

    3. Select Yes to start the setup process

To start process select yes

    4. On the Windows Server 2012 R2 screen, select Install now

    5. For internet-connected devices, select Go online to install updates now (recommended)

How to install updates online

    6. Select the Windows Server 2012 R2 edition you want to install, and then select Next

How to install server 2012

      7. Select I accept the license terms to accept the terms of your license agreement. This will be based on your distribution channel such as (Volume License, Retail, OEM, and so on) and then select Next.

     8. Select Upgrade: Install Windows and keep files, setting, and applications to choose to do an in-place upgrade.

Accept license agreement

    9. The setup reminds you to make sure your apps are compatible with Windows Server 2012 R2, and then select Next.

compatibility check

   10. If you see a page telling you that upgrade is not recommended, you can ignore it and select Confirm. It was put in place to prompt for clean installations but isn’t necessary.

Upgrading windows screen

The in-place upgrade will start, showing you the Upgrading Windows screen with its progress. After the upgrade finishes, your server will restart.

Common Server Upgrading and Migration terms 

  • Upgrading: The process of upgrading to a newer version of Windows Server can vary greatly depending on which operating system you are starting with and the pathway you will be taking. Upgrade, commonly referred to as in-place upgrade, refers to the process of moving an older version of the operating system to a newer version while staying on the same physical hardware.
  • Migration: With migration, you move an older version of the operating system to a newer version of the operating system. This is achieved by transferring to a different set of hardware or virtual machines.
  • Cluster OS Rolling Upgrade: This term means you upgrade the operating system of your cluster nodes without stopping the Hyper-V or the Scale-Out File Server workloads. This feature will allow you to avoid downtime, which would otherwise impact Service Level Agreements. 
  • License Conversion: With license conversion, you convert a special edition of the release to another version of the same release in a single step and with a simple command and the corresponding license key. Take an example; if you are running Windows Server 2016 Standard Edition, you can convert it into Windows Server 2016 Datacenter Edition

When looking forward to upgrading your Windows server, it is recommended you upgrade to the latest version, which is Windows Server 2019. If you run the latest version of the Windows server, it will allow you to use the latest features, including better security and ultimate performance.

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