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Windows Server 2008 End of Support

Windows Server 2008 Now Facing End of Support

On January 14, 2020, Windows Server 2008 reached end of support. This issue is critical news for many enterprises as there are many factors with which to be dealt. This shift may seem worrisome for users, but, in the long run, the change will prove to be the best thing for your business. Each year brings more and differing security threats, so enterprises need different software, security measures, and closer alignment to compliance laws. Here at Agile IT, we want to assist our customers with understanding and implementing these changes. Indeed, we want to help your business take this next step.

Compliance Risks in 2020

Computing in 2020 will, inevitably, pivot around compliance, privacy, and security. The growth of ransomware will continue. New privacy laws have been adopted already, such as the California Consumer Protection Act (CCPA), a new Cybersecurity Maturity Model Certification (CMMC), and end-of-life (EOL) technology upgrades that can creep up on businesses.

If businesses do not keep abreast of what is going on in IT, not only will things become inconvenient, but also new 2020 legal requirements will occur. Research from Vanderbilt University found that cybersecurity issues caused an upward trend in deaths from heart attacks because of time spent battling ransomware attacks and how the hacks complicated patient care.

All enterprises that use technology must obtain security compliance information in 2020. Trends and changes during 2019 have shown that essential compliance risks will be prevalent in 2020.

Windows End of Support

Though it may seem obvious, if your technology is out of date, you must upgrade or replace it. Contemporary SaaS providers reduce the amount of money you spend on improving systems. If you are having problems with managing your software, move to a cloud-based system.

For example, Microsoft products that are ending support include:

  • System Center Data Protection Manager, version 1807 System Center Operations Manager, version 1807 System Center Orchestrator, version 1807 System Center Service Manager, version 1807 System Center Virtual Machine Manager, version 1807
  • Azure Container Service Windows Analytics
  • Windows 10, version 1709 (Enterprise, Education, IoT Enterprise); version 1809 (Home, Pro, Pro for Workstation, IoT Core); version 1809 (Datacenter Core, Standard Core)
  • Visio Services in SharePoint Online
  • Windows 10, version 1803 (Enterprise, Education, IoT Enterprise)
  • Windows 10, version 1903 (Enterprise, Home, Pro, Pro for Workstations, IoT Enterprise); version 1903 (Datacenter, Standard, IoT Enterprise)
  • Lastly, InMage/ASR Scout

However, a full list of products reaching end of support is available at support.microsoft.com.

Windows Virtual Desktop

Windows announced recently that its Virtual Desktop eliminated Microsoft Office 365 ProPlus support for Windows Server 2019. The reason? Microsoft wants its customers to adopt a customer cloud desktop with WVD. Indeed, this move will hasten the relocation of customers’ apps to the cloud. Further, the new Microsoft Azure service provides the virtual desktop infrastructure, along with Remote Desktop Session Host management.

Costs Involved With These Changes?

The impacts that come with the ending of support for specific technologies are:

  • Some costs will accompany security updates, which may have previously been free of charge.
  • Compliance activities will be a bit overwhelming.
  • However, there will be missed innovation opportunities.

If your business is using a Window Server 2008, you will benefit from:

  • Cost savings vs. on-premises
  • Improved security
  • Improved compliance
  • Lastly, the use of cloud innovation to retire technical debt

How to Update and Stay Protected

End of Support

There are several avenues you can take as you become more familiar with the changes and solutions coming your way. For example:


Migrate apps to Azure VMs (Lift and Shift).


Migrate your data to Azure-Managed Instances or VMs (PaaS Services, Containerization).


After your workloads migrate, cloud modernization opportunities are yours.


Move to Windows Server 2016 or 2019.


Move to SQL Server 2017.

Purchase Extended Security Updates

Indeed, users can get three additional years of security updates for Windows Server and SQL Server 2008

The Microsoft Modern Lifecycle Policy

Microsoft will use this policy to cover products and services that are continuously serviced and supported by a company. Your product will remain supported as long as you:

  • Stay current in the servicing and system requirements published for the -product or service
  • You are licensed to use the product or service
  • Lastly, Microsoft currently supports the product or service

Customers will be required to stay up-to-date with changes for these products and services since they may be more frequent and require more attention to upcoming modifications. For those products and services that are governed by the Modern Lifecycle Policy, in most cases, the policy will provide a minimum of 30 days’ notification when you are required to take action to avoid significant degradation to the regular use of the product.

The Evolution of Windows Servers

  1. Earliest version – 2008
  2. Windows Server 2008 R2
  3. 2012
  4. 2012 R2
  5. 2016
  6. 1709 and 1803
  7. Lastly, 2019


Users have two choices when migrating from Windows Server 2008 SQL. You can migrate from Windows Server to on-premises, or you can migrate to Azure. If you choose on-premises, you can upgrade to Windows Server 2016 or 2019, or SQL Server 2017. Also, you will need extended security updates. If you choose to migrate to Azure, you will need to rehost, refactor, and modernize.

Need Some Assistance?

We understand that we have offered up plenty of information. But this is what we do, so we think we can complement the process of end-of-Support issues for your business. For enterprises that wish to remain compliant, they will need to commit themselves to work on making these changes viable. The changing laws must be understood and put into place as soon as possible.

Agile IT knows that a lapse of compliance or an unusable server can mean the risk of litigation and governmental fees. In fact, we can get you started with modern software like Office 365 that has a complete suite of built-in compliance tools and controls. Simplify this journey by calling on our experts who can simplify this process and make your 2020 a winning year.

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