Windows Server Summit 2026 | Part 9: The path to easier Windows Server migration
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In the past, upgrading Windows Server to a newer version was a laborious process. For this reason, companies tend to put it off until the very last minute. However, this creates time pressure, and typically not all servers can be migrated in time. This, in turn, leads to unnecessary security vulnerabilities or additional costs (if ESUs need to be purchased).
But it doesn’t have to be this way. With Windows Server 2025, migration has been significantly simplified. Cloud services are also available as an alternative to temporarily host virtual machines (as part of a transformation). This article discusses the key aspects and possible approaches for migration.
Virtual machines in Azure
Azure offers a wide range of options for deploying virtual machines—different performance tiers, categories for specific use cases, and several ways to reduce ongoing costs. The latter are particularly useful when virtual machines need to be run in Azure over an extended period of time:
| Variant | Description | Usage scenario |
|---|---|---|
| Spot Virtual Machines | Utilizing currently unused compute capacity at a significant discount | Non-critical workloads that can be interrupted and do not require high performance |
| Reserved Instances | Discount on compute costs for long-term commitments with static workloads; potential savings increase with the length of the commitment | Medium- to long-term operation (1–3 years), continuous operation (24/7) |
| Savings Plans | Discount on compute costs for long-term commitments with dynamic workloads; potential savings increase with the length of the commitment | Medium- to long-term operation (1–3 years), flexible operation (e.g., 13 hours a day, 5 days a week, daytime only, etc.) |
In addition, special preconfigured virtual machines are available with certain Microsoft products, such as SQL Server, already preinstalled. The clear advantage here is that the installation and configuration comply with Microsoft’s recommendations. Furthermore, these servers offer potential cost savings and simplified licensing, as the licensing costs are, in a sense, included in the compute costs.
Migration and modernization strategies
Strategies for modernization have now become established, referred to as 6R or 8R depending on their specific characteristics. The following table illustrates the 6R model:
| Strategy | Usage |
|---|---|
| Retire | Outdated application with little or no business value |
| Rehosting | Migration from an on-premises data center to an IaaS service (also known as “lift-and-shift”) |
| Replatforming | Migrating applications to a new runtime environment using PaaS services |
| Refactoring | Restructuring the application code and migrating to microservices |
| Rearchitecting | Updating and expanding the application code to optimize it for cloud environments |
| Rebuilding | Complete redesign of the application on a cloud platform |
Microsoft illustrates possible approaches to this using a decision tree and potential target scenarios.
Migration support in Azure
Microsoft offers a variety of solutions to assist with migration and help you choose the strategy best suited to your specific scenario.
Migration Agent in Azure Copilot
Azure Copilot includes a migration agent that can help you make this decision. It analyzes the application to be migrated and designs a suitable target architecture in Azure that can be implemented immediately.
Azure Migrate
Azure Migrate is the traditional migration solution that has been around for several years and is constantly being refined. It also provides an analysis of the application to be migrated, including a visualization of dependencies. This can be done either agent-based or agentless, depending on the organization’s specific security requirements and the data needed.
For example, complex interrelated server structures can be identified, grouped, and migrated together to avoid issues caused by missing dependencies. Recommendations are also provided for the correct resource sizing in Azure. Resources can be replicated directly. This enables a nearly seamless transition from on-premises to cloud deployment.
Migration from VMware to Azure
Microsoft offers a solution specifically for VMware to ensure the transition is as seamless as possible. This solution is called Azure VMware Solution and delivers VMware technology on Azure, allowing you to continue using existing management solutions and migrate virtual machines directly.
In essence, this allows you to extend your on-premises data center into the cloud. Virtual machines can be migrated first and then modernized or transformed.
Modern Administration with Azure services
Even in the cloud, servers must continue to be monitored, updated, and secured. Microsoft provides the following services for this purpose:
- Defender for Cloud is the central service for Cloud Security Posture Management (CSPM) and ensures, among other things, the protection of Windows Servers using policies in Azure Policy and endpoint security via Defender for Servers. Collected data can be aggregated and viewed and processed in a comprehensive, centralized view.
- Scaling sets can be used to automatically increase the availability and performance of servers as needed. This is suitable, for example, for e-commerce systems that experience very high load at certain times but are barely utilized during other periods.
- Azure Backup can be used to back up servers. Just like other solutions, entire servers or individual data can be restored. Azure Backup also offers protection against ransomware attacks and supports modern security features such as Trusted Boot (coming soon for Windows Server 2025).
- Azure Monitor can be used to monitor system parameters such as CPU, RAM, disk, and network utilization and provides corresponding alerting functions when critical thresholds are reached.
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