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10 key considerations for running Microsoft workloads on AWS

As an ‘AWS Advanced Tier Services Partner’, we help enterprises modernize and migrate their Windows workloads to AWS seamlessly.

Download as PDF 4th August, 2025
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Migrating to the cloud helps enterprises escape the burden of aging infrastructures, steep license costs, and end-of-support deadlines.

Considerations when migrating Microsoft workloads to AWS

  • Whether to bring your own Microsoft licenses or switch to AWS-provided ones, and what the financial difference actually looks like in practice.
  • brillioOne.ai uses AI-driven automation to reduce migration timelines and eliminate manual handoffs across five phases.
  • Why Windows Server containers on AWS can increase infrastructure density and cut compute, storage, and licensing costs significantly.
  • What a free AWS Optimization and Licensing Assessment reveals about hidden cost reduction and rightsizing opportunities in your current environment.

Why should you choose AWS?

Here’s the thing most enterprise technology conversations won’t say plainly: Microsoft licenses are expensive, and they’re designed to stay that way. AWS offers a different model. You can bring your existing licenses through the BYOL pathway, use AWS-provided licensing on a pay-as-you-go basis, or start replacing Microsoft-licensed products entirely with open-source and cloud-native alternatives built specifically for the cloud.

AWS has been running Microsoft workloads since 2008. That’s not a marketing claim. It means the platform has 15-plus years of tuning, tooling, and operational learning for exactly these environments. The breadth of compute options matters here too. With more than 750 generally available, secure, and resizable instance types, organizations can match workloads to the right infrastructure instead of over-provisioning to compensate for rigidity.

And rigidity is expensive. When enterprises simply lift and shift without optimization, they replicate the cost inefficiencies of on-premises infrastructure in the cloud. That’s a migration, not a transformation. The organizations getting the most out of AWS are the ones treating the move as a decision point, not just a destination. Which path makes sense for your Windows Server, SQL Server, or .NET environment? The answer depends on where your licensing agreements stand today, what’s reaching end-of-support, and how much operational burden your teams are carrying. There’s more to unpack here than a single framework can hold.

Why Brillio for your Microsoft workloads on AWS?

We have been credited with being an AWS Advanced Tier Services Partner and an OLA Certified Partner. But the credential worth paying attention to is what it translates to operationally: native support for SQL server, active directory, and the full range of common Microsoft technologies, meaning lift-and-shift is genuinely viable as a starting point rather than a theoretical option.

Our position isn’t to push enterprises toward a single modernization path. The real value is in the range of options available and the expertise to assess which one is right for a specific environment. That includes maintaining full governance and control by creating cloud-based controls that mirror existing on-premises IT governance. For regulated industries, that matters considerably.

For organizations running Windows-based applications on on-premises or EC2 SQL Servers, Our team can assess actual resource use, license status, and application dependencies to build an architecture and licensing strategy grounded in real data rather than estimates. The scope covers everything from shifting workloads to Linux OS on Amazon EC2 to refactoring SQL Server to open-source or cloud-native engines, replatforming to Windows Server containers, and rearchitecting toward event-driven and serverless models.

The question enterprises should be asking isn’t whether migration is possible. The real question is which combination of pathways delivers the fastest return while protecting operational continuity. That’s where the assessment work becomes the starting point, not the end point.

Can you bring your Microsoft licenses to AWS?

Yes, and this is one of the more consequential decisions in any Microsoft-to-AWS migration. AWS is a Microsoft Authorized License Mobility Partner, which means you can bring licenses including SQL Server with active Software Assurance to Amazon EC2 on shared tenancy. The pathway is called BYOL, bring your own license, and for organizations with significant existing investments in Microsoft licensing, it’s often the fastest route to cloud without sacrificing compliance.

BYOL makes the most sense if you want to extend the lifecycle of existing software without additional hardware costs, use current virtual machine images to accelerate the migration, or maintain licensing investments that still have runway. AWS-provided licenses, on the other hand, suit organizations that want to pay as they go with no upfront costs or long-term commitments, let AWS manage licensing compliance entirely, or deploy workloads that need to scale dynamically.

And that dynamic scaling point is more significant than it sounds. Windows Server, SQL Server, Office, and Visual Studio licenses on AWS-provided instances remain fully compliant as your footprint scales up or down. For businesses dealing with seasonal demand, rapid growth, or unpredictable compute requirements, that flexibility has real financial value.

Our team assesses existing license portfolios to identify where cost reduction is achievable by aligning current licenses to AWS deployment models or transitioning to AWS-provided options. The analysis is more nuanced than a simple BYOL-versus-not comparison, and the full breakdown of how that assessment works is worth reading in detail.

Can you automate the migration of your Microsoft workloads?

brillioOne.ai is a suite of AI-driven capabilities designed specifically to accelerate cloud migration across five structured phases. prepare, plan, migrate, operate, and optimize. Each phase is powered by AI-driven intelligence for automation, optimization, and security.

The architectural anchor here is the AWS Well-architected Framework. brillioOne.ai is designed to keep organizations 100% aligned with that framework throughout the migration, ensuring security, reliability, performance efficiency, cost optimization, and operational excellence aren’t afterthoughts added post-migration. They’re built in from the start.

In practical terms, this means readiness assessments and risk analysis in the Prepare phase, AI-assisted roadmap creation and resource allocation in Plan, automated migration tools and data integrity checks during Migrate, continuous performance monitoring and security management in Operate, and cost management with ongoing AI-driven improvements in Optimize.

The value isn’t just speed, though brillioOne.ai does eliminate manual effort and reduce migration timelines measurably. The deeper value is in error reduction and future-readiness. Manual migrations introduce human error at every handoff. Automating across all five phases removes those risks while integrating with AWS-native services to produce an environment that’s not just migrated but architected for what comes next. The full specification of what brillioOne.ai does inside each phase goes well beyond what a summary can capture.

How can you optimize and modernize your SQL Server?

SQL Server Enterprise licensing is one of the most consistent pain points in enterprise IT. The cost is significant, the terms are rigid, and the upgrade cycles create pressure points that often force decisions before organizations are ready to make them well.

On Amazon EC2 deployments, consolidating small SQL Server databases, using SQL Server Developer edition for non-production environments, and applying the Optimize CPU feature can reduce costs by up to 75 percent. These aren’t theoretical savings. They’re achievable with configuration changes that our database experts can identify through an assessment of your actual environment.

Beyond optimization, there are three primary modernization paths. SQL Server on Amazon EC2 with Linux OS eliminates Windows Server licensing fees entirely. Amazon RDS for SQL Server simplifies database management through a fully managed Platform-as-a-Service model, handling backups, patching, and scaling with reduced administrative overhead. And for organizations ready to go further, refactoring SQL Server workloads to open-source or cloud-native database engines offers long-term scalability and flexibility that proprietary licensing simply can’t match.

Our cloud and database teams have deep expertise across all three paths, plus the broader landscape of purpose-built AWS databases suited to specific application types. Choosing the right option requires understanding your current workloads, performance requirements, and long-term application direction. That’s a conversation worth having before the next SQL Server license renewal lands.

Can you run Windows Server containers on AWS?

Containers are more efficient than virtual machines. That’s not a preference. It’s an architectural reality with direct implications for infrastructure density, resource utilization, and cost. For Windows environments specifically, where compute, storage, and licensing costs accumulate quickly, the shift to containerized workloads can deliver savings that compound over time.

AWS supports Windows Server containers across a range of options: self-managed environments on Amazon EC2, fully managed orchestration through Amazon ECS and Amazon EKS, and AWS Fargate for serverless, pay-as-you-go compute that removes the server management burden entirely. With Docker Windows Containers and Kubernetes Windows worker nodes both supported, Brillio can guide customers through the replatforming process without forcing a full rearchitecture of existing applications.

The development lifecycle benefits are equally significant. Automating build, test, and deploy processes through containerized infrastructure frees DevOps teams to focus on product work rather than operational maintenance. And for legacy applications that need to keep running while modernization happens around them, Windows Server containers provide a viable bridge: the application runs on a modern, scalable infrastructure without requiring a complete rewrite.

For .NET applications specifically, Brillio’s replatforming path moves workloads to Windows containers on AWS, increasing infrastructure density while preserving the .NET environment that development teams are already running. The mechanics of how that transition is structured, and the specific AWS tooling involved, deserves closer examination than a summary allows.

What is the top recommendation for running Microsoft workloads on AWS?

Optimize before you migrate. That’s the single most important piece of advice for any organization planning to move Microsoft workloads to AWS, and it’s one that gets overlooked more often than it should.

Lifting and shifting without optimization replicates the cost structure of on-premises infrastructure in the cloud. The savings and efficiencies the cloud provides only materialize when workloads are right-sized, licenses are aligned to actual usage, and the architecture is matched to what cloud-native services can actually do. The difference between an optimized migration and an unoptimized one is often the difference between a measurable cost reduction and a cost transfer.

We offer access to a free AWS Optimization and Licensing Assessment for new and existing customers. An OLA analyzes hardware performance, application dependencies, and existing contracts to generate a tailored migration and licensing strategy. The output is specific: actionable recommendations for both immediate cost savings and long-term optimization opportunities, based on what your environment actually looks like rather than what a standard template assumes.

Two trigger points make this especially timely. If a Microsoft Enterprise Agreement is approaching renewal, or if you’re running Windows Server or SQL Server versions near or past end-of-support, the OLA creates an objective basis for the decisions ahead. It turns a deadline-driven pressure point into a structured opportunity to evaluate what the future state of your IT environment should actually be. The full framework we use to structure that evaluation, across discovery, landing zone creation, and migration phases, is where the real decision-making clarity comes from.

Before you migrate: Six things worth knowing

  • Optimizing before migration, not after, is what separates genuine cost reduction from a simple infrastructure cost transfer.
  • BYOL and AWS-provided licensing serve different needs; the right choice depends on your current agreements and growth trajectory.
  • brillioOne.ai automates all five migration phases, reducing manual errors and keeping workloads AWS Well-Architected aligned throughout.
  • Windows Server containers increase infrastructure density and cut licensing overhead, especially for legacy .NET applications on AWS.
  • End-of-support deadlines for Windows Server and SQL Server are decision points, not just deadlines, and they reward early, structured evaluation.
  • A free AWS OLA assesses your actual environment to generate specific, tailored recommendations rather than generic migration guidance.
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