Description of work: The Department of Housing and Works is upgrading servers currently running Windows Server 2012 R2 and 2016 to the latest Windows Server version compatible with the Department’s applications. The upgrade path (in-place upgrade vs. fresh build and migration) and the target Windows Server version (Windows Server 2025 vs. Windows Server 2022) will be determined on a server-by-server basis. We are seeking a skilled and experienced Windows Server Engineer to lead this upgrade and migration project. The ideal candidate will have a proven track record in similar upgrade projects and possess expertise in Windows Server, Azure, Active Directory, DNS, scripting, automation, networking, and security. Key Responsibilities: • Project Planning and Design: o Assess the current Windows Server and 2012 environments, including virtual hardware, applications, network connectivity and other dependencies. o Assist in the development of a detailed migration strategy and project plan, including timelines, resources, and risk management. o Assist in the collaboration with stakeholders to identify business requirements and ensure alignment with organizational goals. • Implementation and Migration: o Perform in-place upgrades, migrations, or fresh installations of Windows Server as required. o Configure and optimize server roles, features, and services. o Migrate applications, databases, and workloads to the new environment with minimal disruption. o Ensure compliance with security best practices during migration. • Testing and Validation: o Conduct pre- and post-migration testing to ensure functionality, performance, and reliability. o Validate data integrity and system compatibility after migration. • Documentation and Reporting: o Create comprehensive documentation for the upgraded environment, including configurations, processes, and procedures. o Provide regular progress updates and reports to stakeholders. • Support and Troubleshooting: o Address and resolve issues during and after the migration process. o Provide technical support and guidance to IT teams on the new Windows Server environment. • Optimization and Security: o Implement advanced features of Windows Server and enhanced security capabilities. o Ensure the environment adheres to organizational and regulatory security standards.