We get it; change is scary. If you've been running the same operating system for many years, a large-scale overhaul is understandably intimidating.

If you have been putting off the inevitable, it's time to start making some critical decisions. Microsoft is ending support for SQL Server 2008 and 2008 R2 on July 9 and Windows Server 2008 and 2008 R2 on January 14, 2020.

The good news is that, if you are still relying on these systems, you are not alone. It is estimated that about half of enterprise server and database servers are running on the 2008 platforms.

Typically, the end-of-support deadline for enterprise software triggers uncertainty, but it is also an opportunity to evaluate your datacenter strategy. Some of the questions to ask your team include:

  • Will our core line of business applications run on a newer operating system? And what version(s) are supported?
  • Do we still have a maintenance or support agreement with those software vendors to help with the migration/upgrade?
  • Were any key custom applications written by an employee who is no longer with the organization?
  • Is there money in the capital budget for the new hardware required for a server upgrade?
  • What are our long-term plans: are we planning on maintaining our datacenters or are we considering some cloud solutions?

There is no right or wrong plan; the path for your organization depends on the risks/rewards that you are willing to accept.

Do Nothing – This is certainly the least expensive option (in the short run). Yes, you can avoid spending on hardware and migration costs for now; however, many software vendors will only support the most recent versions of their applications. You run the risk of voiding any support agreements plus the ability to upgrade to the newest versions which provide those features and functionalities that your business needs to grow. This route also exposes your company to both security and compliance issues and potential fines.

Purchase Extended Support – For some applications, you may be able to purchase an extended support contract for approximately 75% of the yearly licensing costs. Yes, your systems will stay patched, but you will still be unable to upgrade in order take advantage of the features and benefits that new versions offer.

Upgrade your Datacenter – New hardware coupled with application migrations/upgrades avoid the security and compliance risks of the other two solutions, but they carry serious capital expenditures plus the costs associated with training your staff to manage and run these newer platforms. Additionally, this further entrenches your organization in the on-going hardware refresh cycles.

Move to the cloud – There are multiple cloud solutions available. Perhaps your application’s vendor has a cloud-based version that would allow your team access without having to be in the office. Maybe you want to get out of the datacenter business entirely and move your systems to AWS, Google or Microsoft Azure. These cloud providers offer the platforms (PaaS) and infrastructure (IaaS) to run your servers on a monthly subscription basis while the vendor assumes the burden of maintaining the infrastructure and its availability.

Hybrid cloud – If you are not ready to throw all of your systems into the cloud at once, a hybrid approach may be the ideal solution. This approach preserves your option to develop a cloud migration strategy to reduce your datacenter footprint, while still leveraging the benefits that an IaaS or PaaS solution offer. You might decide to transition systems due for a hardware refresh to the cloud immediately while keeping others on-premises, for compliance, governance or legacy issues. For these systems, an on-premises upgrade let you take advantage of the new security and feature capabilities in Windows Server 2019.

Moving workloads to the cloud allows companies to shift IT costs from the capital to the operational budget. With the subscription model offered, organizations pay only for consumed resources and can scale up and down as needed. Compare this to the on-premises options where hardware is purchased upfront based on four to six-year usage predictions.

End of support can be viewed as either a time of uncertainty or as one of opportunity. High Availability can help you evaluate your options and plan the most appropriate path forward; whether that is a datacenter upgrade, a cloud migration or a hybrid solution. Reach out to begin your path forward. You can also learn more about the End of Support for Windows 2008 and SQL 2008 here: