Dedalus Windows Server Migration and Modernization for AWS

Organizations running Windows Server, SQL Server, .NET applications, Active Directory, and SharePoint on legacy infrastructure face escalating costs, security risks, and end-of-support deadlines. Dedalus delivers a structured professional services engagement to migrate, optimize, and modernize these workloads on AWS - reducing operational overhead, improving performance, and building a secure foundation for future growth.

Phase 1 - Discovery and Assessment (estimated 2-4 weeks)

• Automated application discovery and dependency mapping across servers, databases, and licensing models
• Identification of modernization opportunities using the AWS 7 Rs framework
• Deliverable: Assessment Report with recommended migration strategy, target architecture, and risk profile

Phase 2 - Migration Planning and Execution (estimated 4-12 weeks depending on scope)

• Workloads rehosted, replatformed, or modernized based on assessment findings
• Secure AWS Landing Zone deployment aligned with the AWS Well-Architected Framework
• Migration rehearsals, rollback planning, and compliance validation at each gate
• Deliverable: Migration Runbook, Landing Zone documentation, and post-migration validation report

Phase 3 - Optimization and Continuous Improvement (ongoing)

• Cost reduction through licensing optimization via AWS License Manager
• Performance tuning, high-availability configuration, and operational automation
• Deliverable: Optimization Plan with cost savings analysis and operational recommendations

• Amazon EC2 for compute workloads
• Amazon RDS for SQL Server
• AWS Managed Microsoft AD for identity services
• AWS Systems Manager for operational management
• AWS License Manager for licensing optimization
• Amazon FSx for Windows File Server

Risk mitigation is embedded throughout the engagement lifecycle. Automated dependency mapping, security assessments, compliance validation, and migration rehearsals ensure a controlled transition with minimal business disruption. Secure AWS Landing Zones provide governance, identity management, and operational security from day one.

• Customer must have an active AWS account or be prepared to create one
• Access to existing infrastructure for discovery tooling is required
• Customer assigns a project lead and infrastructure subject matter expert
• Licensing inventory and documentation should be available for assessment
• Scope covers Microsoft workloads (Windows Server, SQL Server, .NET, AD, SharePoint); non-Microsoft workloads and full application rewrites are out of scope

Schedule a discovery call to begin your Windows Workload Assessment. Contact Dedalus to scope your environment and receive a tailored migration roadmap.