Organizations with on-premises Windows Server or SQL Server environments have many compelling reasons to migrate those environments to the Azure cloud. They can reduce capital expense, save on resources, improve security, and take advantage of unlimited scalability, resilience, and security. At the same time, they can become more agile and innovative to drive business growth.

And yet – despite all the upside potential of a cloud migration – some organizations have yet to make the leap. Others have attempted a cloud migration but encountered issues and have been unsure how to move forward within their environment.

There’s no question that some organizations do encounter obstacles when migrating their Windows Server or SQL Server environment to Azure. Here are three of the most common issues we’ve seen, along with some recommendations on how best to overcome them.

1. Unknowns in the on-premises environment

It’s not unusual for on-premises IT environments to become complex and unwieldy over time. As a result, some organizations may not be fully aware of all the current assets in their IT environment when they begin their migration efforts. When a forgotten server running an outdated (or unsupported) software version comes to light in mid-migration, it can complicate the project, slowing progress and requiring more time and effort to address.

How to overcome this obstacle
Before beginning any migration, do a comprehensive inventory and assessment of the on-premises environment. Determine what will be included or excluded from the migration and address any incompatibility issues first.

2. A shortage of in-house cloud migration and management expertise

Cloud migration and management are specialized disciplines requiring experience, tools, and proven methods. IT teams that have worked exclusively in on-premises environments are not well-equipped to perform the migration, increasing the risk of error and slowing the migration process. Post-migration, those same IT teams may not understand how best to manage their new cloud environment; this can cause possible mismanagement or deviation from cloud best practices.

How to overcome this obstacle
Instead of attempting the migration in-house, seek out a migration services provider with a proven track record of success. That services provider will likely have proprietary tools to automate and accelerate migration-related tasks. This approach will have the added benefit of freeing internal IT staff to focus on driving business value. To ensure maximum cost-effectiveness and manageability post-migration, ensure your IT team is trained in advance on cloud management best practices and compliance. In addition, upskill your team on DevOps, Kubernetes, and other skills that will enable you to take maximum advantage of the cloud environment.

3. Project planning issues

Proper planning is key to any successful Windows or SQL Server cloud migration. However, a migration project plan can’t be just a sequence of tasks prioritized by the degree of difficulty or importance to business operations. That approach has the potential to bog down the effort, make inefficient use of resources, and cause post-migration problems that could affect business operations. The project plan needs to account for the full complexity of the undertaking.

How to overcome this obstacle
Put ample strategic thought, time, and effort into developing a meticulous, realistic migration project plan. Organize each server/database migration according to the amount of work required, from basic “lift and shift” (no modifications necessary) to refactoring (some modifications required) to modernization (full conversion from legacy to cloud-native). Consider all interdependencies among database environments and servers and any post-migration ramifications. Prioritize the work so that each completed task builds on the previous one. Arrange activities in the plan so multiple work streams can be performed in parallel and teams are kept productive and on task. Finally, ensure that your project plan is aligned with Microsoft’s Cloud Adoption Framework (CAF) for Azure and Azure’s Well Architected Framework (WAF) to ensure a seamless transition.

Neudesic Cloud Factory is built to address these issues – and more

The challenges of Windows Server and SQL Server migration to the Azure cloud are real and significant. Neudesic’s Cloud Factory is a comprehensive service offering designed to mitigate all the most common risks of cloud migration and post-migration management. Powered by automation and taking full advantage of Neudesic’s deep experience in cloud migration, Cloud Factory leverages prebuilt scripts, dashboards, and preconfigured data governance and security frameworks to make your migration swift, sure, and seamless. To learn more, visit