Windows 2008 Server is a server operating system produced by Microsoft that was released in February 2008. It is the successor of Windows Server 2008 and predecessor of Windows 2008 R2 released in October 2009.

With technology evolving at an ever-increasing rate, it's crucial for organizations to keep their systems up-to-date on all the changes continually. To that end, many are aware that on July 9, 2019, Windows will stop providing extended support for its SQL Server 2008 and 2008 R2. Similarly, on January 14, 2020, the extended support for Windows Server 2008 and 2008 R2 will also end.

This end of support implies that you will no longer receive regular security updates. And even though many people view these regular updates as nothing more than annoyances, they are, nevertheless, critical for your system security. Cyber-attacks are becoming more frequent and more sophisticated with every passing day, meaning that an unsupported system with leave you and your business vulnerable to system infection, malware, ransomware, and other such cyber-attacks. Similarly, it can also take you out of compliance with industry regulations such as the EU's own General Data Protection Regulation (GDPR).

The disruption is an opportunity in disguise. End of support for Windows Server 2008 will allow you to take advantage of cloud technology such as Windows' own Azure. This cloud-based solution will enable your organization to scale up or down more quickly, save on computer power, pay for only what you use, have access to better innovation opportunities, among other such benefits.

Preparing for Windows Server 2008 End of Life

It's not wise to wait and transition only when the end of support comes into effect. Making the transition will take some time, and it's better to make it at your pace rather than being rushed by circumstance. Three steps involve a successful migration from Windows Server 2008 to Azure. These include the Assessment Phase, the Migration Phase, and the Optimization Phase.

1. The Assessment Phase - During this step, you will have to use Microsoft Data Migration Assistant, Azure Migrate, or other such partner tools to make a thorough inventory of your apps and workloads. The next step will be to categorize each of them based on type (Microsoft apps, ISV apps, Custom LOB apps, and Server roles.) Then, classify them based on criticality (Mission Critical, Important, and Normal), and finally by risk (Low, Medium, High). These will help you better plan your migration.
2. The Migration Phase - At the migration step of the process, you can transform critical aspects of your operation by moving away from old platforms. You will need to update your server to Windows Server 2019 to get DevOps and cloud-ready and take your application portfolio to the cloud.
3. The Optimization Phase - Once the migration is complete, you can begin fine-tuning your resources for cost optimization, better management, as well as for security and compliance. With Azure, you can manage your resources and cost, as well as strengthen your security and ensure the compliance mentioned above. Tools such as Azure Security Center, Azure Cost Management, and Azure Advisor will help you manage your cloud resources. With System Center, you can integrate your on-premises workloads with Azure for a seamless and fully optimized hybrid cloud environment.

Microsoft recently announced that they are partnering with Mesosphere to bring the Windows Server ecosystem to the Mesos’ highly scalable and elastic container orchestration world by porting directly to Windows Server. Mesos is one of the most established and proven open source container orchestration technologies, used in very large scale production environments by several Fortune 500 companies. Apart from Mesos, Microsoft already supports Docker Swarm/Compose, Deis, and many others.

Mesos on Windows Server is an open source project and is part of the core Apache Mesos. While this is being developed by both Mesosphere and Microsoft, we’re inviting others in the community to join in the effort. The code will be freely available, making it easy to adopt by all users of Mesos as well as integrate with the Mesosphere DCOS, which is built atop Mesos. The latest version of Mesos on Windows Server is available in the Apache Mesos GitHub today.