Windows Server 2008 Is End Of Life. You Have Options.

By David Ngo

Most IT professionals are well aware that Windows Server 2008 is now end of life, and SQL Server 2008 has been end of life for a few months now. This means no more product updates or security updates. It also means you’re not taking advantage of the latest Windows Server or SQL Server features and you’re still using technology that was released 12 years ago. That’s a lifetime in tech years.

At Inspire 2019, Microsoft estimated that 60% of its server install base was still running Windows Server and SQL Server 2008. That’s 24 million instances. Does this apply to you? Odds are you still have one or both running in your environment.

Earlier last year, Gartner called out the risks these end-of-life deadlines posed1 in the hopes of inspiring businesses to act:

  • A significant portion of business-critical apps depend on Windows Server 2008
  • Lack of legacy OS support and security updates jeopardizes the ability to meet regulatory, compliance and security requirements
  • Without a migration plan, applications and infrastructure services that depend on Windows Server 2008 will be at an increased risk of compromise due to security vulnerabilities

We wholeheartedly agree. Gartner also predicted that “by 2022, 50% of organizations that do not have a migration plan in place for Windows Server 2008 will be forced to migrate due to a security incident, with limited time, higher cost and higher risk.”

Next steps and options

1. Do nothing

While this may be the “path of least resistance” right now, it not efficient. Not only do you face increasing security risks, support costs will also exponentially escalate because you are no longer on a mainline product. We’re talking many times more expensive.

2. Extended security updates – a stopgap

Far from a permanent solution, a short-term investment in Extended Security Updates might be worth your while if you anticipate a long or delayed migration. Microsoft has made this available for both products for a maximum of three years from the end-of-life date. These updates, for an added cost of course, only cover “critical” and “important” security fixes.

3. Upgrade to newer on-premises

If the plan is to stay on-premises, you need to make plans to migrate to a newer, supported edition. This brings you greater innovation and more built-in security features, but the migrations can be arduous and lengthy, especially given you are three versions back from the latest Windows Server 2019. Further, any migration effort will result in noticeable downtime and disruption.

4. Migrate to Azure

Rehosting Windows Server 2008 in Azure (or Azure Stack) is the friendliest option giving you needed breathing room to modernize and update, while benefiting from security updates as well as access to cloud capabilities – and minimizing disruption to the business. Benefits of migrating to Azure include:

  • Three years of Extended Security Updates for Windows Server 2008 included, making it possible to stay secure and compliant
  • Automatic security updates and no-charge upgrades in Azure
  • Ability to use existing licenses and save up to 80% on Azure Virtual Machines with the Azure hybrid benefit and Azure Reserved Virtual Machine Instances
  • Access to the tools in Azure to modernize your applications and focus on innovation with new fully-managed services

(Note that moving to AWS or another cloud does not extend your support or provide the opportunity for license savings).

Cloud migration strategy

If you’ve decided on rehosting in Azure, you’re going to need a migration strategy. As some organizations can take months (even years) to migrate operations to the cloud, a fast, flexible data migration solution is important.

Metallic™ Core Backup & Recovery empowers IT with an automated way to easily migrate to Azure with just a few clicks. This includes network bandwidth optimization to lessen time and network charges, and data encryption in transit – with added benefit of ongoing protection of the data migrated. For more information, please visit

If you are one of the many still running Windows Server 2008 or SQL Server 2008, it’s time to actively plan your migration, not to mention consider the move to Microsoft Azure – using a third-party tool like Metallic to migrate in just a few clicks.


  1. Gartner, “How to Prepare for Windows Server 2008 End of Support”, March 2019