Migrate Windows Server 2008 to Azure

Windows Server 2008/R2 is now no longer supported by Microsoft. The 14th January 2020, marked the end of extended support for Windows Server 2008/R2.  The risks of remaining on unsupported Windows Server 2008/R2 are not to be taken lightly. Security and compliance lapses, customer loss, damaged reputation, and missed opportunities are just some of the risks of remaining on unsupported Windows Server versions.

Many organisations use this milestone as an opportunity to reassess their infrastructure and consider other options, such as migrating to the cloud. With the right strategies, organisations can make sure they are protected, that their infrastructure is secure and that their technology stack is future-driven.

So, what are the reasons to migrate Windows Server 2008/R2 to the cloud? Moving on-premises Windows Server 2008/R2 to Azure provides many benefits, including instant scalability, reduced operational costs and automated security updates. Here are 3 big reasons to migrate Windows Server 2008/R2 to Azure.

Save money

Eliminate capital investment with Azure, by utilising Microsoft’s security, redundancy and disaster recovery for your IT systems, without the expense of secondary infrastructure. Save with free extended security updates, Azure Hybrid Benefit, and optimised infrastructure.

For example, organisations can save 31% costs over five years moving on-premises Windows 2008/R2 to Azure. (Source: Guide –“End-of-Support for Windows Server 2008/R2: How to use end-of-support as an opportunity to transform and move to the cloud”).

Microsoft has several end-of-support offers to incentivise organisations using Windows Server 2008/R2 to move these workloads to Azure. These offers include saving up to 85% when you combine Azure Hybrid Benefit for Windows Server and SQL Server on Azure Virtual Machines (VMs). Organisations can also migrate Windows Server 2008/R2 to Azure and gain three more years of extended security updates at no extra charge.

Security and compliance, such as GDPR

Gain the benefit of critical security updates to eliminate business interruptions and loss of data. Migrating your applications to Azure enables you to strengthen your security posture and consistently meet compliance requirements. Azure contains industry-leading security measures and privacy policies to safeguard data in the cloud, including the categories of personal data identified by the GDPR.


Grow your environments with data, analytics and the cloud. Innovate quickly and efficiently while minimising up-front costs. As you migrate, you can embrace the innovation available in Azure to modernise your applications. You can focus on business innovation with fully-managed services such as Azure SQL Database, Azure App Service and Azure IaaS.

Discover our guide “End of Support for Windows Server 2008/R2, which will give you all the information you need on migrating Windows 2008/R2 to Azure.

Alternatively, visit our Business Continuity Hub, to gain access to a wide range of helpful resources.