Windows Server 2008 End of Support (Questions and Answers)

Windows Server 2008 End Of Support

Unfortunately, all good things must come to an end — and on January 14, 2020, Microsoft will be stopping mainstream service for their highly popular Windows 2008 Server. If you are one of the millions of organizations who are still using this secure and highly stable solution, it may be time to look for other options before maintenance becomes an even greater challenge. The current Windows Server 2019 was released in November 2018 and since this is the fifth software release since Windows Server 2008, it’s not surprising that Microsoft has finally decided to deprecate mainstream support. Here are the answers to your burning questions about Windows Server 2008 end of support transitions.

What Does End of Service Mean for Windows Server 2008?

While the end of support period (EOS) for Windows Server 2008 is looming, that doesn’t mean the platform will stop working on January 14, 2020. It simply means that Microsoft will no longer be required to provide support and patches unless your organization has a specific contract in place to maintain support. All software and hardware have an effective lifecycle and Windows Server 2008 has been in a period of maturity for many years. This planned EOS period means that non-security updates, free support options, online technical content updates and free security updates on-premises will be halted by the Microsoft support team. Microsoft recommends that organizations immediately review options to shift to cloud-based options such as Microsoft Azure as this allows businesses an additional 3-year window of updates that are classified as Critical or Important by the Microsoft support teams. There are also options that allow customers to purchase Extended Security Updates at a premium to provide additional time to perform a migration.

What Are the Dangers of Windows Server 2008 Being Unsupported?

The security vulnerabilities alone should be reason enough to drive your business to make a decision to shift to a new solution. Cybercrime accounts for over billions of dollars of expenses and lost revenue for businesses each year, and a lack of security updates and patches can provide hackers with a door directly into your most valuable digital systems and information. With Accenture estimating that cybercrime could cost businesses over $5.2 trillion in the next 5 years, creating a secure environment for the backbone of your business is more crucial than ever before. That staggering statistic is based on the possibility of losses primarily to major health and life sciences organizations such as pharmaceutical companies. The potential for industrial espionage is significant when you consider the value of pharma knowledge and the capture of personally identifiable information.

What Happens to My Business When Windows Server 2008 Support Ends?

System vulnerabilities are nothing new for technology professionals, but many security-minded teams recommended freezing technology at Server 2008 as a stable and reliable solution for their business in years past. Now that the support is due to be deprecated, data managers are looking for ways to upgrade their server solutions or move directly to the cloud. Cloud-based solutions provide you with the flexibility and scalability that is needed for today’s modern organizations while offering a high level of security to combat the continual threats to your systems and data.

What Steps Should I Take Before Windows Server 2008 End of Support Date Arrives?

It’s not unusual for server upgrades to take quite some time, so it’s prudent to begin researching alternatives immediately. Begin with an audit of all the servers that are being used to determine the scale of the upgrade as well as any possibilities for consolidation. Server migration can cause a significant impact not only to your budget, but also to your users. If you do not already have a server migration strategy in place, now would be the time to map out those recommendations with a trusted technology partner. Finding a partner with a great deal of experience in Windows Server 2008 migrations or upgrades can help you avoid many of the land mines that might otherwise have a negative impact on your project.

What Are Best Practices for Windows Server 2008 Upgrades or Replacement?

While some organizations choose to go directly to the cloud for their server needs, there are other options for your business. You could decide to simply upgrade to a newer, stable version of Windows Server on-premise or utilize a private cloud or other hybrid solution to meet the needs of your business and stay within your budgetary requirements. Working with a technology solutions provider gives you the added firepower of external backup and recovery mechanisms in case something goes dramatically wrong during your transition period or in the event of a cyberattack.

Whether you decide to push forward with a full migration using your internal team or decide to work with a technology solutions partner, it’s crucial that you complete your investigations and make a plan of attack to migrate away from Windows Server 2008. There is an extremely high-risk factor when you stay with an unsupported software platform, making it all too easy for cybercriminals to infiltrate your weakened digital defenses.


  • Joe Cannata

    Having a reliable and enthusiastic partner in the realm of IT services and solutions is essential for achieving continuous growth by implementing effective technological strategies. Our owner, Joe Cannata, is wholeheartedly dedicated to helping clients optimize their technology to gain a competitive edge in their industries. At Techsperts, Joe leads a team of highly dedicated professionals who are fully committed to providing exceptional IT services and solutions. With his extensive expertise and hands-on experience, Joe ensures that clients receive unparalleled support and guidance for their IT projects. You can trust Techsperts to elevate your business systems and remain at the forefront in today's fiercely competitive business landscape.

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