5 questions to ask before migrating Windows and SQL Server 2008 to the cloud

five question marks

Most midsized companies have relied on Windows and SQL Server 2008 for the past decade to run essential business applications. Now that these long-trusted products are coming to end-of-life (EOL) status, businesses still running these systems face hard decisions.

It’s a major challenge for many organizations, and a full-blown crisis for some.  But I’ve always felt that within every crisis there’s opportunity, and opportunity does present itself at this inflection point.

The good news: Microsoft has been helping organizations buy time by providing extended updates for these server platforms if they move to Azure. This will ensure customers get vital security updates and provides three years extended support to re-envision these workloads. The prospect of simply porting the applications running on these systems to Azure has become very attractive to some shops. Not only can they postpone upgrading or rewriting software, which may not run on new versions of Windows Server or SQL Server, they also can retire old out-of-warranty hardware.

Many organizations will choose a lift-and-shift approach to move the operating systems, SQL Server, and application code as-is into the Azure cloud. While this approach minimizes effort and risk, the introduction of a WAN connection between the client and the server may cause performance and user experience issues if not addressed through other means, such as a WAN caching appliance or deploying a remote access solution such as Remote Desktop Services or cloud-hosted VDI.

This EOL event also creates a major inflection point for looking at infrastructure holistically, and can be used as a catalyst to move toward cloud maturity by upgrading, replacing or rewriting the applications running on EOL systems. Most people are familiar with the 5 Rs of cloud migration (or 6, depending on which blog you read): Rehost, replatform, repurchase, refactor and retire.

Before you decide which approach to take, ask the following questions to make sure your organization makes the best possible decision:

  1. What’s the end goal? And how long will it take? If the only business issue is keeping the applications running with the least amount of cost and risk, then a lift and shift to Azure makes sense. Depending on the size and complexity of the application, it will take a few weeks to a few months. If your organization needs to increase agility, look at which applications can be replaced or refactored/re-architected to run on a cloud-native PaaS solution, or take advantage of cloud native architectures such as microservices. Complex or custom applications may require a combined strategy of lift and shift first, followed by rewriting or replacing the application.
  2. What help do I need to get there? Evaluate your organization’s cloud and Microsoft Azure experience. If you lack experienced Azure staff, or want to keep your team focused on strategic initiatives, consider using third-party consulting and support services to manage the migration. Even with the operating system and applications in the cloud, you’ll still need skilled administrative and security resources to operate on Azure.
  3. Does moving my department’s app to the cloud align with the company’s ongoing cloud strategy? Very often line-of-business managers have ownership of an important business application, but aren’t privy to the organization’s big picture cloud strategy and how their app fits in. The organization may already have a cloud footprint, an existing cloud migration initiative, or cloud resources that can be leveraged. Likewise, the IT organization must communicate these capabilities and strategies to the business.
  4. What are the financial and security risks of each path? The lift-and-shift approach keeps the business moving, but it doesn’t deliver any additional capabilities on its own. In comparison, replatforming may allow for an upgrade to the latest OS and application code, with the latest business functions. Re-architecting applications to be cloud-native, or replacing them with a SaaS solution, could create new opportunities and increase business agility – moving the organization farther along the cloud path.
  5. How does moving the app to cloud impact the company’s compliance mandates? Look at the decision through a compliance lens and determine which path best aligns with compliance mandates or goals. This will vary by industry, but a company that must comply with PCI standards, for example, should discuss options with a PCI Qualified Security Assessor (QSA) to address needs both now and in the future. It is not uncommon to find companies that don’t necessarily have to comply with PCI but do so because it’s a good set of best practices for operations and security. Talking to a PCI QSA could be a smart move.

Look at the impending EOL of Windows and SQL Server 2008 as much more than just another deadline. It’s a great opportunity to enhance your cloud strategy. By choosing the right approach to migrating these old systems to the cloud, companies can modernize, improve application performance and lock down security and compliance. While this will require some investment in time, money and skills, the potential benefits will be well worth the effort.

Chris Lavelle is Vice President, Client Services at DXC Concerto Services. An expert in cloud service delivery and support, Chris has more than 20 years of experience in IT consulting and leadership of highly technical and service-related teams. Chris manages cloud advisory, migration and strategic delivery services for Concerto customers and partners, with an unyielding focus on driving efficiency, smooth integrations and exceptional service.


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