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Top 10 Questions Customers Ask About Migrating Microsoft Workloads to AWS

Amazon Web Services (AWS) has been a leader in helping customers migrate their Microsoft workloads to the cloud since 2008 - longer than any other cloud provider. As an expert in this field, Mission Cloud, an AWS Migration and Modernization Competency partner, has successfully migrated thousands of Microsoft workloads to the cloud for various customers. Choosing AWS for your migration means joining millions of satisfied customers who benefit from improved performance, enhanced security, reduced total ownership costs and flexible licensing for Windows Server, SQL Server and .NET workloads.

AWS and Mission Cloud offer comprehensive support for your cloud migration needs, whether transferring individual workloads or entire data centers. Both Mission Cloud and AWS stand out with our extensive range of migration and modernization services, enabling you to harness the business advantages of the cloud quickly.

But how do you know if migrating Microsoft workloads to AWS is the right choice for your organization, and what does it take to provide a seamless transition? Let’s take a closer look at the 10 most common questions businesses face across migration topics ranging from automation options and cost optimization strategies to SQL Server, .NET workloads, Windows Server containers and other key areas. We’ll also include top recommendations for customers managing these workloads on AWS.

Why Should You Choose AWS to Run Your Microsoft Workloads in the Cloud?

Customers consistently choose AWS for its extensive experience running Microsoft workloads, more so than any other cloud provider. This expertise enables AWS to offer superior operational capabilities on a large scale. Additionally, AWS is the go-to choice when it comes to licensing flexibility for Microsoft workloads. Microsoft licenses can quickly become costly, and challenging to understand and manage. AWS provides adaptable licensing options for your Microsoft workloads that can be managed directly within your infrastructure account control pane. This flexibility includes bringing your own licenses or using a pay-as-you-go model without contracts or agreements.

AWS also stands out from a modernization perspective as well. It offers the opportunity to move away from traditional Microsoft-licensed products and towards specialized cloud-based technologies. This shift can help avoid the restrictive terms and high costs of Microsoft licensing.

Mission Cloud has assisted hundreds of customers in migrating and modernizing their Microsoft workloads with AWS and offers its expertise to you as well. Check out Mission Cloud’s case studies for more insights into how we have successfully helped customers.

Can You Bring Your Microsoft Licenses to AWS?

Bringing your existing Microsoft licenses to AWS can be a powerful option for some businesses. As a Microsoft License Mobility Partner, AWS enables you to transfer your existing licenses, such as SQL Server with active Software Assurance, into their cloud environment on Amazon Elastic Compute Cloud (Amazon EC2). This approach, known as Bring Your Own License (BYOL), can be ideal for several reasons. It allows you to fully leverage the benefits of the cloud while keeping your current licensing investments. You can also extend the life of your software without the need for additional hardware expenses and expedite your migration to the cloud by using your existing virtual machine images.

When you opt for BYOL, you can unlock significant savings in licensing costs, particularly as you customize your server or instance sizes according to your cloud requirements. If you prefer a more straightforward approach, you can choose AWS instances that already include licensing fees. This option ensures that your Windows Server, SQL Server, Office, and Visual Studio licenses remain compliant without the burden of managing them yourself.

Suppose your priorities include a flexible, pay-as-you-go model without upfront costs or long-term commitments, the option to deploy workloads that scale efficiently with your needs, and complete control over billing for license-included instances. In that case, AWS-provided licenses might be more suitable. This choice also relieves you from the complexities of licensing compliance, as AWS manages it for you.

Their Microsoft licensing FAQ is a valuable resource for a deeper understanding of Microsoft licensing on AWS. Additionally, AWS offers a complimentary Optimization and Licensing Assessment (AWS OLA) to fine-tune your on-premises and cloud environments. This service ensures you pay only for what you use while maintaining compliance with third-party licenses.

How Can You Reduce Your Dependency on Microsoft Licensing With AWS?

Many new and established customers seek ways to free themselves from the restrictive and expensive licensing terms associated with Microsoft products. The goal is to cut costs, enhance security, and boost the cost-efficiency of their Microsoft applications. This is where AWS and Mission Cloud come into play.

AWS empowers you to innovate faster. How? You can replace Microsoft-licensed products and applications with open-source alternatives and cloud-optimized technologies. This can lead to significant improvements in your projects' speed and efficiency. Here are some effective strategies:

  • Switching from Windows Server to Linux for a more flexible and cost-effective operating system.
  • Migrating applications from the .NET Framework to the more modern .NET platform.
  • Breaking down large, unwieldy monolithic applications into more manageable and efficient microservices.
  • Adopting DevOps practices using container and serverless technologies for faster and more reliable software deployment.
  • Moving your data storage and management to Amazon Aurora and other specialized databases designed for optimal performance.

If you're considering a move away from traditional licensing to embrace more freedom and cost savings, Mission Cloud is ready to guide you through this modernization journey. They provide the expertise and support necessary to smooth the transition and benefit your organization.

How Can You Optimize the Cost of Your Windows Server Workloads on AWS?

With over 600 secure and resizable compute instances, AWS offers the largest selection of instances compared to other cloud providers. These instances are optimized for various use cases, including CPU, memory, storage and networking capacity.

While this flexibility allows you to choose the right resources for your applications, over-provisioning on compute instances can result in unnecessary costs and resource consumption. To help you lower the total cost of ownership (TCO) for your Windows Server workloads on AWS, consider the following recommendations:

  • Identify the right instance type. If you haven’t done an AWS OLA, start today. This free assessment will evaluate your Windows environment and identify ways to reduce costs and run your resources more efficiently. AWS also has rightsizing tools to help you identify over-provisioned resources.
  • Use optimization tools for Windows Server workloads. AWS offers a broad range of tools that can help you gain insight into your current and future AWS costs:
    • AWS Compute Optimizer offers valuable insights and suggestions for optimizing workloads, which can result in cost savings up to 25 percent.
    • AWS Trusted Advisor can help you save costs with actionable recommendations by analyzing usage, configuration, and spend.
    • AWS Cost Explorer lets you view and analyze your costs and usage. For example, you can view data for the last 12 months, forecast how much you will spend for the next 12 months, and get purchase recommendations.
  • Select the right Savings Plan. Savings Plans are based on a flexible pricing model that can help you reduce your bill by up to 72% compared to on-demand prices, in exchange for a one- or three-year hourly spend commitment. AWS offers three types of Savings Plans: Compute Savings Plans, EC2 Instance Savings Plans and Amazon SageMaker Savings Plans.

With the right approach, you can uncover substantial savings from server cost optimization. Mission Cloud has helped many customers with identifying and realizing cost savings after migrating their Microsoft workloads to AWS. For our customer Intruity, Mission Cloud right-sized their C# and .NET workloads post migration to AWS, leading to over 25% savings, improved security posture and increased resiliency compared to its on-premises Windows servers.

Can You Automate the Migration of Microsoft Workloads to AWS?

Several tools help automate your migration to the cloud.

AWS Application Migration Service

This free service can help simplify and expedite your migration by automatically converting your source servers from physical, virtual or cloud infrastructure to run natively on AWS. It also reduces costs by allowing you to use the same automated process for a wide range of applications, without changes to the applications, their architecture or the migrated servers.

AWS Migration Hub Strategy Recommendations

Easily build a migration and modernization strategy for your applications running on premises or in the AWS Cloud. The Strategy Recommendations feature automates the manual process of analyzing each running application — its process dependencies and technical complexity‌ — ‌to reduce time and effort spent on planning and speed up your business transformation on AWS.

AWS Migration Hub Orchestrator

The Orchestrator feature of the AWS Migration Hub provides a single location to run and track your migrations. It simplifies and automates the migration of servers and enterprise applications to AWS and offers templates to create customizable migration workflows to fit your unique migration requirements.

How Can We Optimize and Modernize Our SQL Server Workloads on AWS?

The high cost of Microsoft licenses for SQL Server, especially SQL Server Enterprise edition, is a concern for many customers.

Here are a few money-saving recommendations for SQL Server on Amazon EC2 deployments:

  • Consolidate small SQL Server databases
  • Use SQL Server Developer edition for non-production environments
  • Use the Optimize CPU feature to save up to 75%

Deploying SQL Server on Amazon RDS offers a fully managed relational database service that simplifies the setup, operation and scalability of your SQL Server deployment while significantly reducing your operational overhead. 

For specialized operations with your SQL Server data, consider exploring fully managed purpose-built cloud databases. AWS offers a wide range of 15+ database engines that support various data models, including relational, key-value, in-memory, document, wide column, graph, time series and ledger. AWS also offers open-source alternatives like SQL Server on Linux and Babelfish for Aurora PostgreSQL.

A high-functioning cloud environment enables you to scale when necessary. For instance, VBO Tickets partnered with Mission Cloud for a more cost-efficient architecture to meet demand. Learn how Mission Cloud moved VBO Tickets’ MS SQL databases to Amazon RDS, rebuilt its CI/CD pipeline with Jenkins and upgraded all of its legacy Windows instances.

Can We Run Our .NET Applications on AWS?

AWS has been supporting .NET in the cloud since 2008. You can run both your legacy .NET Framework and modern .NET applications on AWS.

Here are some of the ways you can run .NET on AWS:


The simplest way to migrate .NET applications to AWS is to rehost them using AWS Elastic Beanstalk or Amazon EC2.


With containers, you can bundle your .NET application with its dependencies and configuration, making it easy to port between on-premises and the cloud. AWS offers a variety of container services to host your containerized .NET Framework application on Windows or your modern .NET application on Linux. You can use the AWS App2Container tool to generate a container image for your application.


You can modernize your .NET application to a cloud-based architecture to maximize scale and reliability, take advantage of serverless compute and run on Linux at a reduced cost. The Porting Assistant for .NET tool helps you port your code to modern .NET, and the AWS Microservice Extractor for .NET tool simplifies the process of transforming your monolithic application into microservices.

Can We Run Windows Server Containers on AWS?

Yes, you can run Windows Server containers on AWS, and here are five reasons why you should.

Enhanced Efficiency

Containers are more efficient than virtual machines, providing better isolation and optimizing application placement. This maximizes resource utilization and reduces costs.

Streamlined Development Lifecycle

Automating the stages of the development lifecycle, such as build, test and deploy, simplifies processes for DevOps teams. This automation frees up time for innovation and accelerates time-to-market.

Modernizing Legacy Applications

By leveraging Windows Server containers and running them on modern infrastructure, you can modernize legacy applications. This improves scalability, security and maintainability, ensuring your applications remain up-to-date.

Rapid Scalability

Containers enable rapid scaling, making them ideal for applications that require quick expansion or cloud bursting. This flexibility ensures your applications can handle increased demand efficiently. For example, the e-learning platform, Let’s Go Learn, needed to containerize after explosive growth. Mission Cloud designed a microservices architecture that reduced database response time for customers from seconds down to milliseconds and lowered infrastructure costs by 25%.

Skill Development

AWS offers free immersion days to upskill development teams on container technology and DevOps practices. This valuable resource helps teams stay updated and proficient in containerization.

How Can AWS and Mission Cloud Help Us Handle End-of-Support Challenges for Windows Server and SQL Server? 

Forced decision points like end-of-support (EOS) events create a unique opportunity for you to think about the future state of your business, evaluate options and alternatives and determine which path is right for you. Here are a few ways AWS and Mission Cloud can help.

Holistic Evaluation

When considering cloud providers for migrating, optimizing and modernizing EOS workloads, it's crucial to assess factors like price/performance, reliability, technology offerings, innovation pace, flexible licensing options and streamlined processes.

Assess, Optimize, and Migrate

Mission Cloud and AWS often begin migration and modernization initiatives with an AWS OLA to evaluate your current on-premises and cloud environments. This assessment considers resource utilization, licensing considerations, and application dependencies. Mission Cloud assists in optimizing the migration process, and AWS Systems Manager Automation runbooks automate upgrades for EOS workloads.  

Legacy Windows Server Applications

AWS offers the End-of-Support Migration Program for Windows Server. This program helps migrate legacy Windows Server applications to the latest supported versions on AWS without requiring any code changes. It addresses compatibility and dependency issues effectively.

Modernization and Innovation

AWS offers the most robust support and has accelerated the modernization of customers’ legacy applications, infrastructure and databases. Mission Cloud offers professional and managed services that help customers  break free from the software upgrade and refresh cycle. For example, after several years on-premises, ATCC learned that its data centers were shutting down, meaning 31 production servers, a DR environment and 8 TB of data were at risk. With Mission Cloud’s support, the entire process of migrating to AWS was completed in under 2 hours with zero downtime.

What Do You Recommend for Customers Wanting to Run (or Already Running) Their Microsoft Workloads on AWS?

You should optimize your Microsoft workloads‌ — from both a licensing and infrastructure standpoint‌ — ‌to run in the cloud. If you simply lift and shift your workloads from on-premises to the cloud without optimizing, you may miss out on the savings and efficiencies the cloud provides. Here are some additional recommendations.

License Optimization

Use the free AWS OLA program to assess and optimize your on-premises and cloud environments based on actual resource usage and third-party licensing. Mission Cloud can provide a migration and licensing strategy that right-sizes your resources, offers a clear AWS roadmap, and eliminates unnecessary costs.

Timing Considerations

If your Microsoft Enterprise Agreement is up for renewal or you're using Windows Server or SQL Server versions reaching end-of-support, it's an ideal time to conduct an AWS OLA assessment.

Ongoing Infrastructure Optimization

Continuously optimize your infrastructure to achieve cost savings. AWS Compute Optimizer analyzes the configuration and utilization metrics of your AWS resources. It provides optimization recommendations to reduce costs and improve workload performance by provisioning instances that match your exact demands.

Accelerate Your Modernization With AWS Services and Programs and Mission Cloud Solutions

To streamline your workload modernization journey, rely on a trusted AWS Partner like Mission Cloud. AWS Partners who hold the AWS Migration Competency have demonstrated technical proficiency and proven success in delivering solutions that accelerate your journey to AWS.

AWS also offers the AWS Migration Acceleration Program (MAP), an outcome-driven methodology based on their extensive experience migrating thousands of customers to the cloud. MAP combines best practices, tools, expertise, financial incentives and solutions delivered by AWS Partners to simplify cloud adoption and help customers achieve their business goals faster. Mission Cloud is highly experienced working within this methodology and consistently delivers leading results amongst AWS MAP partners.

By aligning to AWS best practices such as MAP, Mission Cloud can work in tandem with your in-house IT teams to ensure a smooth, efficient cloud transition.

Utilizing the foundational methodology of MAP, Mission Cloud applies a three-phase approach to modernize your enterprise workloads:

  1. Assess: The migration readiness assessment identifies gaps along the six dimensions of the AWS Cloud Adoption Framework: business, process, people, platform, operations and security. This allows you to determine the capabilities required to migrate and build a TCO model. 
  2. Mobilize: The mobilize phase creates an operational foundation for migration, with the goal of fixing the capability gaps that were identified in the assessment phase. This step accelerates migration decisions by providing clear guidance.
  3. Migrate and modernize: In this final phase, you execute the migration plan developed during the mobilize phase. After testing applications, you can begin migrating workloads to AWS, then optimizing for performance and spend.

When Experience Matters, Customers Choose AWS

AWS is the world’s most comprehensive and broadly adopted cloud platform, offering over 200 fully featured services from data centers globally. Millions of customers‌ — ‌including the fastest-growing startups, largest enterprises and leading government agencies‌ — ‌use AWS to lower costs, become more agile and innovate faster.

AWS has significantly more services, and more features within those services, than any other cloud provider, making it faster, easier and more cost-effective to move your existing applications to the cloud and build nearly anything you can imagine.

Mission Cloud is exclusively partnered with AWS and 100% of our engineering teams are AWS certified. As a next-generation cloud services provider, we combine managed and professional services to help businesses migrate, manage, modernize and optimize their AWS environments at every stage of their cloud journey.

Give your Microsoft applications the infrastructure they need to drive the business outcomes you want.

Modernize your workloads with Mission Cloud today.



  1. What are the specific compliance considerations when migrating regulated Microsoft workloads like those in healthcare or finance to AWS?

When migrating regulated Microsoft workloads like those in healthcare or finance to AWS, specific compliance considerations include ensuring the architecture meets industry standards like HIPAA for healthcare or PCI DSS for finance. AWS provides compliance resources and services that help maintain security standards and regulatory requirements, facilitating secure and compliant migrations.

  1. How does AWS handle data sovereignty issues when migrating Microsoft workloads from regions with strict data residency laws?

AWS addresses data sovereignty issues by providing the option to select the geographic region where data is stored and processed, complying with local data residency laws. For Microsoft workloads, AWS ensures that data stays within the chosen region, which helps meet the legal requirements of countries with strict data sovereignty regulations.

  1. What are the long-term support options from AWS for migrated Microsoft workloads, especially for those no longer supported by Microsoft?
  2. AWS offers long-term support options for migrated Microsoft workloads, even for those no longer supported by Microsoft, through the AWS End-of-Support Migration Program (EMP) for Windows Server. This program assists customers in migrating legacy Microsoft applications to newer, supported versions on AWS, providing them with continued security and compliance.

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