Windows Server 2008 EOL (End of Life)

Windows Server 2008 EOL

Microsoft Windows Server 2008 and 2008 R2 moved past their End of Life (EOL) last  January 14, 2020. This has serious implications for companies that use these servers for virtualization solutions. It’s important to understand what these are and what you should do to minimize or completely avoid unnecessary business risk. 

It’s Actually Called End of Support

windows server 2008 eolIf we want to be accurate about it, the right term for what many are referring to as Windows Server 2008 (and 2008 R2) End of Life is really called End of Extended Support, or simply End of Support (EOS). What this means is that, when the date in question arrives, Microsoft will no longer release patches or security updates for these two products. This can cause security policy and regulatory compliance issues.

Security and Compliance Implications

The absence of security updates leaves your Windows 2008 servers (as well as the applications running on them) exposed to threats that exploit known vulnerabilities. Security updates that normally address known security vulnerabilities are now gone after EOS, unless your organization has purchased Extended Security Updates (ESU), which qualifies it to receive updates until 2022, or a period of three years from EOS. If you have migrated your Windows 2008 Server-based applications to Azure, you are also qualified to receive ESU for the same period.    

Because data privacy/protection laws and regulations (such as HIPAA, GLBA, PCI-DSS, and GDPR) are closely intertwined with cybersecurity, an unpatched server could result in non-compliance and, in turn, potentially lead to onerous fines and penalties. Microsoft has already released several security updates for Windows Server 2008 since EOS. If you have not availed of ESU or have not migrated to Azure, your organization may potentially pay huge penalties for staying on Windows Server 2008. 

Impact on Virtualization Solutions

Just like many other solutions that run on Windows Server platforms, virtualization solutions like Citrix Virtual Apps and Desktops and Parallels® Remote Application Server (RAS) are seriously impacted by any impending Windows Server EOLs. Any unpatched vulnerability in the platform could compromise these solutions if they’re running on it. That’s why when an EOL or EOS date draws near, companies scramble to plan for migrations.

Windows Server 2008 EOL Migrations: Easier Said Than Done

Migrations are usually unavoidable—there’s no question about that. However, doing a migration is not as straightforward as it appears. First of all, these exercises are quite expensive and complex. Some applications could even break if you forcefully migrate them to another (or newer) platform. That’s why most companies prefer to have a longer grace period. They need ample time to plan, execute, test, and validate upgrades and migrations.

Extending Windows Server 2008 EOL Security Updates via Azure

The good news is that Microsoft is providing a way to extend those security updates for free. Security updates can be extended to your Windows Server 2008 and 2008 R2 for three more years if you migrate your Windows Server 2008/2008 R2 virtual machines to Azure, Microsoft’s cloud computing platform. Those three additional years will give you enough time to prepare thoroughly before upgrading.

Problem with Citrix

Unfortunately, if you’re using Citrix, it would be difficult to take advantage of this opportunity. That’s because Citrix Virtual Apps for Windows 2008 and Citrix Virtual Apps for Windows Server 2008 R2 will both reach their own End of Extended Support (EOES) on January 14, 2020.

The Parallels RAS Advantage with Windows Server 2008 EOL

You’ll be in a better position if you’re using Parallels RAS. Parallels RAS continues to support Windows Server 2008 and 2008 R2. What’s more, Parallels RAS itself is also built to run on Azure. So if you’re using or intend to use Parallels RAS, you can take advantage of Microsoft’s offer and enjoy three more years of security updates for free.

Avoid the issues that accompany Windows Server 2008 EOL. Try Parallels RAS now.


Microsoft | Prepare for Windows Server 2008 end of support
Microsoft | Extended Security Updates FAQs
Insentra | Citrix EOL Schedule – The Dates you must know
VirtualWarlock | Citrix Is Finally Ditching Windows Server 2008 R2 and Windows 7
Acutec | What are the business benefits of Microsoft Azure?