Best practices when migrating Windows Server to Azure

Read the latest whitepaper on Whitepapers Online titled,

Read the latest whitepaper on Whitepapers Online titled, "Best practices when migrating Windows Server to Azure"


As companies prepare for the end of support for Windows Server 200 and 2008 R2 in January 2020, companies have an opportunity to transform the way they manage their workloads. Through the migration of the Windows Server to Azure, they can significantly reduce costs, besides reducing the time to market as well as improve security and scalability. A successful and smooth migration requires meticulous planning and execution. Read the following whitepaper targeted at engineers and system administrators to guide them on every stage of the migration.

End of Support for Windows Server 2008 and 2008 R2

Since their launch a decade ago, the Windows Server and SQL Server 2008 and 2008 R2 have been very popular with organizations worldwide. However, both editions are reaching the end of support by the following dates:
  • SQL Server 2008: July 2019
  • Windows Server 2008: January 2020
End of support means that software users will no longer receive security updates. This signifies exposure to security attacks which could also create issues for compliance with industry regulations such as GDPR and the FedRAMP, among others.

How to Move from Windows Server 2008 to Azure

Microsoft will provide numerous benefits related to the extension of the Windows Server support, licensing and upgrading. These benefits include:
  • Migration with extended security updates
  • Option to upgrade at no additional cost
  • Free assessment for Azure migration
  • Usage of existing Windows Server licenses

Migrations Tips and Tricks

Microsoft provides a simple three-step migration strategy to help with cloud migration. They include assessment, migration and last but not least, optimization.

How to Assessing Workloads

A cloud migration commences with careful planning and phases while approaching execution. It is crucial to determine the workloads, their dependencies and the best candidates for Azure migration. An assessment helps in the identification of the on-premise VM sustainability for Azure. Some of the properties to consider before creating an assessment are storage type, Azure offer and Hybrid benefit, sizing criteria, performance history, etc. A few other factors to keep in mind are given below:
  • Microsoft Assessment and Planning Toolkit
  • Azure Migrate
  • How to calculate application risk

How to Organize Workloads

Businesses can organize their inventory into four categories of apps and workloads such as Microsoft applications, custom applications, Microsoft-partner applications and servers that run key workloads.

Using Migration Best Practices

A well-defined migration effort will determine the right approach for requirements, best-defined per the application workload. Companies must also consider factors like tiers, application dependencies, and network connectivity such as firewalls, subnetting and Windows Server roles.

Importance of Optimization

It is important to remember that goal migration is never the final step. Optimization ensures that the new software meets all the security and governance requirements. This includes enhanced performance and cost-effectiveness. The practice of optimization streamlines cloud resources to improve performance and security and maximize ROI.

Key Takeaways from "Best practices when migrating Windows Server to Azure"

  • How to assess existing infrastructure to identify the priorities of migration
  • How to choose the right migration path for a business
  • How to optimize workloads for functionality and reduced costs
Download this whitepaper to gain invaluable insights into how companies can gain numerous benefits by following the best practices during the migration of Windows Server to Azure.

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