This article was originally written by Avanade alum Jose Chavez.

Is your company on the fence about migrating your datacenter to the cloud? Or would you like to migrate—if only you could avoid what might be a complex process with unpredictable expenses? Either way, now might be an ideal time for your migration to the cloud—for a reason you might not expect: the imminent end-of-service for Windows Server 2008 and SQL Server 2008. Microsoft will end extended support for both Windows Server 2008 Service Pack 2 and Windows Server 2008 R2 Service Pack 1 in just over a year, on January 14, 2020. It will end extended support for SQL Server 2008 and SQL Server 2008 R2 even earlier, on July 9, 2019.

With the 2008 code base comprising as much as 50% of the enterprise server and database estate, these deadlines should be of concern to most organizations. Typically, the end-of-support deadline for enterprise software signals uncertainty. This time, that risk is balanced by the potential reward: the opportunity to implement a datacenter strategy that could position your organization for greater competitiveness and growth.

If you’re still running the 2008 Microsoft versions, you need a plan that carries you beyond the expiration dates, one that considers both 1.) which software versions you’ll adopt to replace your 2008 software and 2.) where you’ll run them. Of course, Windows Server and SQL Server aren’t the only software you have to worry about. While your COTS applications should run with little or no trouble on upgraded systems, your custom applications may need more work.

There’s no single right plan; the right choices for you depend on which tradeoffs leave you in a stronger position. Your key options include the following:

• Status quo/do nothing—While this is least expensive in the short run, that’s all you can say for it. Your security and compliance exposure soars, and you lose third-party app vendor support as well as the ability to run new apps and technologies that require modern platforms.
• Extended security upgrades—It’s easy to run what you have with new patches, but you don’t eliminate security and compliance issues. Costs are 75% of licensing cost per year for up to three years. And you’re still increasingly unable to run new apps and technologies.
• On-premises upgrade—An in-place or fresh-build upgrade avoids ESU expenses and some risk exposure, but has costs of its own, requires new skills and app remediation, and does nothing for your cloud strategy.
• Hybrid-cloud upgrade—Adopting Azure IAAS and PAAS in the cloud and Azure Stack on-premises avoids ESU costs and qualifies for Microsoft incentives. Better, it enables app modernization and reduces risk. You still need new skills and face app remediation risk and licensing/transition costs.

For a multifaceted approach, you also need to consider the order in which you upgrade software and migrate platforms—or whether you’ll do better with a big-bang that encompasses both moves. For example, if your hardware is also reaching end-of-life, your priority might be to transition legacy systems to the cloud while planning a move to Windows Server 2019 as a subsequent step. Microsoft Azure is always a good choice as a cloud destination and now it’s an especially good choice for organizations dealing with end-of-support. That’s because Microsoft will continue to provide Azure customers with the critical security updates they need for their software.

For many companies that have hesitated to move to the cloud, this option reduces current barriers to cloud migration. Companies already running part of their environment on Azure gain a new way to address any under-spent Azure commitment by making further migration more attractive.

On the other hand, you may need to maintain your SQL Server 2008 datacenter on-premises for now for reasons that could include governance, compliance or legacy issues. You could still take advantage of the security and feature capabilities in Windows Server 2019 via an on-premises Windows Server 2019 upgrade. Moreover, this choice would preserve your option to develop a hybrid cloud/on-premises datacenter later on that reduces the datacenter footprint, maximizes opportunities in the cloud and meets on-premises needs.

To help you design and implement your datacenter strategy, Avanade offers Windows Server 2008 and SQL Server 2008 End-of-Support Fixed Fee Migration offerings, which include both an Azure migration path and a Windows Server 2019 on-premises upgrade path. These give you the options you need for your datacenter exit strategy, whether you want to lift-and-shift to the cloud now or reduce your on-premises risk now while planning a migration that makes fuller use of cloud capabilities.

With the Azure Migration path, Avanade can design your Azure subscription and then migrate your choice of 100 Windows Servers and 25 SQL Server databases or 250 servers and 50 databases in 12 or 16 weeks, respectively. With the Windows Server 2019 on-premises upgrade path, Avanade helps you create a custom Windows Server 2019 image and deploy it in an automated manner to your choice of 100 servers and 25 databases or 250 servers and 50 databases in 12 or 16 weeks, respectively.

End-of-support can be an uncertain time. But this time it can be the best time to advance your datacenter and cloud-migration strategies, reduce cost and risk, and set the stage for greater business growth.