Windows Server 2008/2008 R2 is Nearing the End of Its Days

Windows Server 2008/2008 R2 is Nearing the End of Its Days

By on Mar 3, 2019 in Technical

The popular server operating system will soon be phased out, meaning it’s time for businesses still running the operating system to start planning for the future.


At the end of last year, we wrote a blog about the impending end of support (EOS) date for Windows 7. You can read that blog here if you’d like. The Windows Server 2008 family of operating systems is also approaching their end of support dates, scheduled for January 14, 2020.

What does end of support mean? It’s a term used by Microsoft to indicate that beyond that date, the software won’t receive any more updates or patches. Here are the most important reasons why running Windows Server 2008/2008 R2 past the EOS date is dangerous:

  • Security and Compliance Vulnerabilities – When you’re running an unsupported operating system, hackers know exactly where your vulnerabilities are, and you’re almost completely powerless to stop them exploiting those vulnerabilities. For organizations that have compliance requirements like HIPAA or PCI, running Windows Server 2008/2008 R2 Server past its EOS date could lead to audits, fines, or even lawsuits.
  • Lost Functionality – New line-of-business software is built to take advantage of the latest hardware and operating systems. Running an unsupported operating system makes keeping up with the newest features and breakthroughs almost impossible, which puts your company at a competitive disadvantage.
  • Infrastructure Instability – With an out of date operating system, there’s a much greater chance that new hardware or cloud services won’t be compatible with your existing systems. This not only affects system efficiency, but could also lead to crashes, lost data, and downtime.

Each of the problems mentioned above applies to any unsupported operating system. These issues are doubly serious for operating systems on servers, which are literally at the core of your business. Now that you understand the dangers, what’s the best way to address this problem? There are three main options.

Option 1 – Move to Microsoft Azure

Microsoft is enthusiastic about getting users onto its hybrid cloud platform, called Microsoft Azure. To incentivize companies to move their Windows Server 2008/2008 R2 workloads to the cloud, they’re offering 3 free years of continued support to companies that do, a plan they call Extended Security Updates. This option lets you migrate your applications to the cloud without making any changes to them and provides you with a grace period to move to a newer operating system. During this three-year period, your Windows Server 2008/2008 R2 systems, now running in the cloud, will continue to receive regular support from Microsoft.

Option 2 – Move to the Latest Windows Server On-Premises

Some businesses may want to keep their applications and workloads on premises. For those businesses, the way toward greater security and reliability is either an in-place upgrade or migration. Moving to the latest version of Windows Server offers many features, like enhanced virtualization and security.

If you choose to upgrade on-premises, you’ll have a few more decisions to make, such as how you’d like to upgrade.

  1. In-Place Upgrade – This option installs the new operating system on the same hardware as the old. When upgrading from Windows Server 2008/2008 R2, you’ll likely have to upgrade to an interim version, Windows Server 2012, before you make the leap to Window Server 2016 or 2019.
  2. Migration – A server role migration that migrates your old operating system and applications to new hardware or virtual machines, testing them individually during the migration process.

Of course, these options have different advantages and disadvantages that must be weighed to find the right one for your business. Which of your network services can make a smooth transition to the cloud? Are your complex line-of-business applications ready for the latest version of Windows Server? These are some of the questions you’ll need to address during an on-premises migration.

Option 3 – Extended Security Updates for On-Premises

Not ready to make the switch right now? Microsoft recently announced that Windows Server 2008/2008 R2 are eligible for extended security updates for on-premises installs. To receive this support, you must have a Software Assurance or Enterprise Subscription agreement with Microsoft. Unlike the options above, this is not designed to be a permanent fix, but can give businesses that have large or complex Windows Server 2008/2008 R2 deployments more time to plan and execute their migration to a newer operating system.

The Windows Server Upgrade Process

Upgrading a server operating system is a long process that includes careful planning. Properly migrating a server to a new operating system will require backing up sensitive data, restructuring existing services to prevent disruption, and potential changes to the underlying hardware infrastructure, to name just a few. There are three main phases to the upgrade:

The process begins with an assessment of your infrastructure and software applications to look for potential incompatibilities.
This is where the work happens. Using tools like the Microsoft  Development Toolkit, your technology partner or in-house staff gets you to the newest version of Windows Server.
With your new operating system installed, the last step is ironing out any problems with your applications and making sure all your devices and employees are on the way to better productivity.


During a server migration, typical business concerns like backorder time and the availability of qualified engineers all apply. So, plan your migration as early as possible to avoid logistical issues and make sure that your IT staff or technology partner has the capacity to help you make a smooth transition.

We’re Your Team of Experienced Migration Pros

Operating system migrations are some of the most challenging, sensitive tasks that an IT team can embark on. If something goes wrong during the process, you could experience hours or days of lost productivity.

That’s why we strongly recommend you find a technology partner like Astute Technology Management to help with your migration to a newer operating system. We can help you with every stage of the process, from the earliest planning and auditing stages, straight through to the continued support that keeps your systems running smoothly.

If you have any questions about the Windows Server 2008/2008 R2 migration process, or would like to know how we can help you streamline that process, feel free to contact us at any time! We love helping businesses in Columbus, Ohio and Cincinnati, Ohio make the most of their technology.

Want to learn more about the managed IT services model? Click here to read our complete guide!