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Upgrade to Windows Server 2016 or consider other options?

As the release date for Windows Server 2016 draws near, will your organization decide to upgrade or go another route?

With Windows Server 2016 expected to be released in the third quarter of 2016, organizations of all sizes should...

begin considering when, how or if they will migrate to this new version. While many organizations will undoubtedly make the transition to Windows Server 2016, there are a number of factors that should be considered as part of the decision-making process.

Windows Server 2016 migration considerations

The key to determining whether an upgrade to Windows Server 2016 is appropriate for an organization is a thorough analysis of how much the migration will cost and what the organization will get for its money. Keep in mind that the costs include more than just licensing. You'll want to account for any training expenses, the hours the IT staff spends on the upgrade and any required hardware purchases.

The benefits derived from a Windows Server 2016 migration vary from one organization to the next. These benefits can range from replacing a severely outdated OS to leveraging new features, such as containers. In any case, the benefit must be significant enough to justify the costs.

As you contemplate the costs and benefits of an upgrade, there are two things to keep in mind. First, an upgrade does not have to be an all-or-nothing decision. It is perfectly acceptable to upgrade some servers, but not others.

The second consideration is that an upgrade might not always be suitable. Windows Server 2016 may be incompatible with a particular application an organization uses or one of the Windows Server features the business relies on may have been discontinued in Windows Server 2016.

Migrating from older Windows Server versions

Although most organizations will not have an urgent need to upgrade to Windows Server 2016, those that are running older versions of Windows Server, such as Windows Server 2008 or Windows Server 2003, should carefully consider the risks associated with continuing to use these aging OSes. In doing so, it is important to separate legitimate risks from marketing hype.

Server products have a limited lifespan during which Microsoft provides support. Windows Server 2003 and Windows Server 2003 R2 reached their end-of-life (EOL) in July 2015. Windows Server 2008 and Windows Server 2008 R2 reached the end of their mainstream support in January 2015. Extended support is available until they reach EOL in January 2020.

The benefits derived from a Windows Server 2016 migration vary from one organization to the next.

A server product's EOL does not mean that the operating system will cease to function on a certain date. Those still running Windows Server 2003 will tell you that the OS continues to operate normally, even after Microsoft discontinued support for it.

Even so, there are two important reasons why it is best to avoid using an outdated OS. First, when there's a problem, you can't call Microsoft for help. In such a situation, an organization will need to try to fix the problem itself or turn to a high-priced consultant. Needless to say, using an unsupported product in a production environment violates long-established best practices. On a more practical level, no one wants to explain to the boss that an outage is being prolonged because essential software is no longer supported.

The second reason why an organization should avoid running an outdated OS relates to security. Microsoft does not create security patches for a product once it reaches its EOL. This means that when security vulnerabilities are discovered, Microsoft will not provide a patch or any official method for addressing the vulnerability. As such, organizations that continue to run the outdated OS are putting themselves at an extreme risk of being hacked.

Is Windows Server 2016 the best choice?

As organizations ponder their upgrade roadmap, it is important to remember that upgrading to Windows Server 2016 is not the only option. For many organizations, an upgrade to Windows Server 2016 will indeed be the best choice. For example, if an organization is currently running an older version of Windows Server, transitioning to Windows Server 2016 is likely the smoothest, least problematic upgrade option. Transitioning from one version of Windows Server to another involves less of a learning curve than in migrating to a competing platform, and Microsoft provides tools and documentation to assist with the migration process. Even so, other options are available.

One such option is to transition to an open source operating system. Microsoft has begun offering much broader Linux support than what was available in the past. Recently, for example, Microsoft said it will offer a version of SQL Server that runs on Linux.

Another option is to retire aging application servers and turn to the cloud. In the software as a service (SaaS) model, application vendors host their products and handle all of the updating. With SaaS, however, a business is dependent on the vendor to reliably provide that software anywhere and at any time. Plus, SaaS users pay ongoing subscription fees. 

Next Steps

Decide if Windows Server 2016 is right for your enterprise

Windows Server 2003 upgrade mistakes to avoid

Migrating to the cloud from Windows Server 2003

Upgrade Windows Server 2012 R2 cluster nodes with Cluster Rolling Upgrade

This was last published in July 2016

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