Keeping up with end-of-support and end-of-life dates is always challenging, but it’s necessary to ensure your business continues to receive security patches and other important fixes in critical software.

For Windows Server 2008 and 2008 R2, the end of support date comes early next year: January 14, 2020. Given the number of machines you likely have running Windows 2008, now is the time to plan your strategy. It’ll be worth your time and effort. Besides keeping systems secure, updating your software is likely to save you money and provides access to new tools that support business innovation.

A Path Away from Windows Server 2008

There are two options for retiring your Windows Server 2008 systems, either moving to the cloud (Microsoft Azure), or upgrading on premises to Windows 2012 and possibly continuing to Windows 2016. In either case, Microsoft suggests a 3-step process for upgrading your Windows Server 2008 inventory.

1. Assess

First, you need to evaluate your Windows Server 2008 and 2008 R2 machines. Once you know the applications and server roles running on each instance, you can decide whether you will keep the servers on premises or migrate them to the cloud. Splitting servers between premises and cloud is also an option.

You’ll want to rank the servers that need to be upgraded in terms of priority and risk. Business-critical instances should be migrated first, because they can least-afford any impact from failures in the unsupported software. You’ll also need to identify any dependencies and data flows to understand if there’s any broader impact or ripple effect once you upgrade.

If you decide that now’s the time to switch to cloud, you should spend additional time to evaluate whether you want to leverage additional cloud services to improve your user experience or provide additional value to the business.

2. Migrate

This is the grunt work of executing the move. Ideally you will leverage tools that reduce the manual work and also reduce the risk of errors. If you chose the Azure path, database migration can be made easier with Azure Site Recovery and Azure Database Migration Service.

3. Optimize

It’s a great feeling when your machines successfully boot up with the new version of the software, but getting the best result requires taking additional time to optimize configuration settings. You’ll also want to make sure you review your operational processes to ensure you’re providing the necessary support with the minimum effort. Multiple tools in the cloud help you manage cloud resource costs and security; on premises, Microsoft System Center Configuration Manager provides assistance.

Executing upgrades and migrations can take time, both due to the need to exercise care and validate every machine after its upgrade as well as simply the number of machines to be upgraded. Make the process faster and reduce the chance of errors with upgrade support from Prescient Solutions. As a Microsoft Partner, we’ve got the expertise and experience to move you to a supported platform and make sure your technology is properly set up to support your business. Contact us to learn more about why and how you should upgrade from Windows Server 2008.