Windows Server Migration: AWS, Azure, On-Prem

April 27, 2023


Windows server migration and upgrade presents an application modernization opportunity via a cloud solution, such as AWS or Azure, which offers benefits including security, flexibility, and potential cost savings. Windows servers are widely used by organizations to handle different operations such as Active Directory, file and print services, web services, and application services. Windows servers at end-of-life (EOL) no longer receive technical support, updates, or patches making them vulnerable to cyber-attacks and affecting the stability and performance of business operations. In this blog, we will discuss different ways to migrate your Windows servers to the cloud, specifically to Azure and AWS.

Windows Server Uses

Windows Server 2008, 2012, 2016, and more recent versions have over a billion users with varying use cases based on the organization’s needs, including:

  • AD Directory: Allows a server to act as a domain controller, handling all user account authentication.
  • Application Server: Windows Server can host applications accessed by users across a network.
  • Networking: Can manage network addresses and related services such as DNS, DHCP, and IPAM.
  • Print: Can manage network printers and print jobs as a print server.
  • Remote Access: Provides secure remote access to a network via VPN and RADIUS server.

Migration: Cloud vs On-Premises

The following table highlights advantages of running Microsoft Server workloads in the cloud over on-premises solutions: 

Windows Server Migration Criteria



Scalability  Easily scalable Limited scalability
Cost-Effectiveness Pay-as-you-go High upfront costs
Security Robust security Limited security
Accessibility Access from anywhere Limited accessibility
Disaster recovery Built-in capabilities Manual process
Support 24/7 support  Limited support
Maintenance Automated updates and patching Manual updates and patching

Windows Server Migration Options

  • AWS Cloud Migration

AWS offers a range of services to migrate Windows Server workloads to the cloud, including the Server Migration Service (SMS), which enables organizations to automate the migration of on-premises servers to AWS. Additionally, AWS provides a fully managed file storage service, Amazon FSx for Windows File Server, which can be used to migrate on-premises file servers to the cloud. Other services such as Amazon RDS can be used to migrate databases, and AWS Application Discovery Service can be used to identify applications running on servers to be migrated.

  • Azure Cloud Migration

Azure also provides a range of services to migrate Windows Server workloads to the cloud, including Azure Migrate, which provides a centralized hub to assess and migrate on-premises servers to Azure. Additionally, Azure provides a fully managed file storage service, Azure Files, which can be used to migrate on-premises file servers to the cloud. Azure Site Recovery can be used to replicate and recover on-premises virtual machines to Azure.

  • Hybrid Cloud Migration

Both Azure and AWS offer hybrid solutions that let businesses distribute workloads between on-premises and cloud environments. This is particularly useful for legacy systems, compliance requirements, or latency-sensitive applications. Azure Stack and Azure Arc allow running Azure services on-premises or other clouds, while AWS Outposts enables running AWS infrastructure and services on-premises. Additionally, AWS offers tools like Direct Connect and VPN for secure connectivity between different environments.

[download_after_email id=”5277″]

Windows Server Upgrade: Cloud Cost

The cost of migrating to AWS or Azure varies based on the size and complexity of the workload being migrated. However, both AWS and Azure offer pay-as-you-go pricing models, which can provide cost savings over traditional on-premises solutions. The TCO (Total Cost of Ownership) calculator for AWS and the pricing calculator for Azure can be used to estimate the cost difference between cloud and on-premises solutions.

Upgrade Comparison: Azure vs AWS

Windows Server Update



Compute services Offers Virtual Machines, App services, Container instances, and Azure functions Offers EC2 instances, AWS Lambda, and Elastic Beanstalk
Database Services Offers SQL Database, Cosmos DB, MySQL, PostgreSQL, and SQL Server Stretch Database Offers Amazon RDS, Amazon DynamoDB, and Amazon Aurora
Migration Tools Provides Azure Migrate  AWS Server Migration Service 
Hybrid Capabilities Offers Azure Arc  Offers AWS Outposts 
Support Provides Azure Support to troubleshoot issues and provide guidance Provides AWS Support to receive technical assistance and resources


Choosing the right platform for running Windows Server workloads is an important decision that can greatly impact the efficiency and cost-effectiveness of your business. AWS and Azure cloud platforms offer many advantages over on-premises solutions, including scalability, cost-effectiveness, robust security, accessibility, disaster recovery capabilities, and automated maintenance. The right platform will depend upon your particular use cases and requirements of your company, and all factors should be properly considered before making a choice.