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Transitioning from Windows Server 2008 Before Support Ends

The challenges of addressing obsolescence are small compared with the potential pitfalls of hanging onto technology after support has ended. This is an especially salient topic at the moment, as Windows Server 2008 and 2008 R2—which have powered tens of thousands of businesses over the past decade—are on the way out. Microsoft support expires on January 14, 2020.

Since the change was announced in 2012, we’ve designed and implemented cloud migration plans for hundreds of clients. We also know that a lot of companies haven’t yet made the transition. We get it—change is daunting, and the idea of moving from on-premises hosting to a subscription cloud service comes with its own concerns (and significant benefits, but we’ll get to that).

Conquering those concerns isn’t just a good idea but a business imperative. Your enterprise IT infrastructure becomes much more stable and your business more productive when you jettison end-of-life technology.

We’d never recommend trying to wring further use out of a product after support has ended, and there are a lot of good reasons for that. Here’s why we urge you to get moving now:

  • End of support means more than losing access to Microsoft’s support team—although that alone is a monumental drawback. It also signals a hard stop for security upgrades, patches, and bug fixes, putting your data at risk of infiltration. When newer systems are issued a fix, cybercriminals see opportunity in end-of-life systems that may share the patched vulnerability. If you’re on an older system, you’re practically inviting hackers to help themselves to your data.
  • You may be legally obligated to upgrade. If you’re working in a heavily regulated industry, relying on obsolete technology may leave you vulnerable to fines—or worse—if a data breach occurs and can be connected to your outdated tech.
  • As goes Windows Server 2008, so goes software compatibility. Any additions or upgrades going forward will be optimized for Azure or Windows Server 2016, meaning the best-case scenario is that you make do with slow-running applications. Productivity nose-dives while employees wait—and wait. And wait.
  • Your legacy applications become a drain on time and maintenance dollars. When buggy old software fails, remediation efforts quickly become more costly than the migration would have been.

Within each of those pitfalls lie tremendous expenses that could have been avoided. The safer, more cost-effective answer to the looming end of support is to migrate to the cloud. Microsoft Azure presents significant advantages over on-premises hosting, not least of which is the security firepower that the service can offer. No individual business can claim those resources. Constant vigilance on the part of the cloud-service provider frees up your internal resources to focus their skills elsewhere.

For most organizations, a cloud service also presents notable gains in reliability, scalability, ease of backup and recovery, and flexibility. So how to get there from here? With a holistic cloud strategy.

We’ve guided businesses of all kinds through the process of cloud migration. Doing so is an essential element of our IT consulting practice, and it presents clients with invaluable insights into opportunities for streamlining the data environment and better utilizing resources. Any migration starts with a thorough inventory of your environment, which sometimes produces some eye-opening revelations and always facilitates a plan that keeps the process moving in the most efficient and effective way possible—with minimal disruption to your operations.

During this phase, we work with you to prioritize your assets and identify architectural dependencies or other potential issues so that your migration proceeds in the manner that most makes sense for your business—and without surprises. We’ll also use this phase to determine where things go and how they get there because many clients choose a hybrid approach that utilizes Azure and an on-premises server upgrade. With the inventory complete, we can work with you to plan for rehosting workloads, and which applications require refactoring or a rebuild.

We craft a migration strategy and timeline that works for you, and we make it happen smoothly, with meticulous attention to security concerns throughout. When the move is complete, we can work with you to weave Azure’s expanded and upgraded capabilities into your operation, so that your migration does more than just address technology expiration but enhances the way your teams work together.

Windows Server 2008 and 2008 R2 have served our clients well for more than a decade. Now it’s time to bid it farewell (or say goodbye to your peace of mind). We make moving to the cloud manageable with a well-established protocol that keeps your business secure and keeps work humming along, all in service of a giant leap in innovation and security.

We’ve helped hundreds of organizations through their own seamless transitions. Talk to us about yours before Windows Server 2008 support screeches to a halt. Reach out today for a free consultation with our team.