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Windows Server 2008 end of life: Is Azure the right path?

Time is almost up for support for your Windows Server 2008/2008 R2 workloads. Microsoft would like you to migrate those VMs to Azure, but is that the best choice?

As the Windows Server 2008 end of life inches closer, enterprises should consider which retirement plan to pursue before security updates run out.

As of Jan. 14, Microsoft will end security updates for Windows Server 2008 and 2008 R2 machines that run in the data center. Organizations that continue to use these server operating systems will be vulnerable because hackers will inevitably continue to look for weaknesses in them, but Microsoft will not -- except in rare circumstances -- provide fixes for those vulnerabilities. Additionally, Microsoft will not update online technical content related to these operating systems or give any free technical support.

Although there are benefits to upgrading to a newer version of Windows Server, there may be some instances in which this is not an option. For example, your organization might need an application that is not compatible with or supported on newer Windows Server versions. Similarly, there are situations in which it is possible to migrate the server to a new operating system, but not quickly enough to complete the process before the impending end-of-support deadline.

Microsoft has a few options for those organizations that need to continue running Windows Server 2008 or 2008 R2. Although the company will no longer give updates for the aging operating system through the usual channels, customers can purchase extended security updates.

You can delay Windows Server 2008 end of life -- if you can afford it

Those who wish to continue using Windows Server 2008 or 2008 R2 on premises will need Software Assurance or a subscription license to purchase extended updates. The extended updates are relatively expensive, or about 75% of the cost of a current version Windows Server license annually. This is likely Microsoft's way of trying to get customers to migrate to a newer Windows Server version because the extended security updates cost almost as much as a Windows Server license.

The other option for those organizations that need to continue running Windows Server 2008 or 2008 R2 is to migrate those servers to the Azure cloud. Organizations that decide to switch those workloads to Azure will receive free extended security updates for three years.

Servers often have multiple dependencies, and you will need to address these as part of the migration planning.

Know what a move to Azure entails

Before migrating a Windows Server workload to the cloud, it is important to consider the pros and cons of making the switch to Azure. The most obvious benefit is financial and gives you a few years to run this OS without the hassle of having to pay for extended security updates.

Another benefit to the migration to Azure is a reduction in hardware-related costs. Windows Server 2008 was the first Windows Server version to include Hyper-V, but many organizations opted to install Windows Server 2008 onto physical hardware rather than virtualizing it. If your organization runs Windows Server 2008/2008 R2 on a physical server, then this is a perfect opportunity to retire the aging server hardware.

If your Windows Server 2008/2008 R2 workloads are virtualized, then moving those VMs to Azure can free up some capacity on the virtualization hosts for other workloads.

Learn about the financial and technical impact

One disadvantage to operating your servers in Azure is the cost. You will pay a monthly fee to run Windows Server 2008 workloads in the cloud. However, it is worth noting that Microsoft offers a program called the Azure Hybrid Benefit, which gives organizations with Windows Server licenses 40% off the cost of running eligible VMs in the cloud. To get an idea of how much your workloads might cost, you can use a calculator and find more details at this link.

Another disadvantage with moving a server workload to Azure is the increased complexity of your network infrastructure. This added complication isn't limited just to the migrating servers. Typically, you will have to create a hybrid Active Directory environment and also create a VPN that allows secure communications between your on-premises network and the Azure cloud.

Factor in these Azure migration considerations

For organizations that decide to migrate their Windows Server 2008 workloads to Azure, there are a number of potential migration issues to consider.

Servers often have multiple dependencies, and you will need to address these as part of the migration planning. For instance, an application may need to connect to a database that is hosted on another server. In this situation, you will have to decide whether to migrate the database to Azure or whether it is acceptable for the application to perform database queries across a WAN connection.

Similarly, you will have to consider the migration's impact on your internet bandwidth. Some of your bandwidth will be consumed by management traffic, directory synchronizations and various cloud processes. It's important to make sure your organization has enough bandwidth available to handle this increase in traffic.

Finally, there are differences between managing cloud workloads and ones in your data center. The Azure cloud has its own management interface that you will need to learn. Additionally, you may find your current management tools either cannot manage cloud-based resources or may require a significant amount of reconfiguring. For example, a patch management product might not automatically detect your VM in Azure; you may need to either create a separate patch management infrastructure for the cloud or provide the vendor with a path to your cloud-based resources.

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