Windows Server Upgrade Engineer/Admin

Core Windows Server Upgrade Skills Proven experience performing in‑place upgrades from Windows Server 2016 to 2019 and/or 2022 Strong understanding of Windows Server upgrade paths, edition compatibility, and licensing implications Ability to assess and remediate pre‑upgrade blockers (deprecated roles, drivers, legacy applications) Hands‑on experience reviewing and resolving setupact.log / setuperr.log issues Knowledge of supported .NET, PowerShell, and role dependencies across Windows Server versions Experience validating post‑upgrade OS health (services, roles, performance, event logs) VMware vSphere & Virtual Machine Operations Experience working with VMware vSphere / ESXi virtual machines Ability to safely perform: VM snapshots (pre‑upgrade and rollback planning) Disk space checks and expansion if required VMware Tools verification and upgrades Understanding of vCPU, memory, and virtual hardware compatibility with newer Windows Server versions Pre‑Upgrade Planning & Risk Mitigation Ability to: Run and interpret Windows Upgrade Readiness checks Verify application and vendor support for target OS Confirm backup validity and recovery options Experience documenting: Upgrade plans Rollback procedures Success criteria and validation steps Familiarity with change management and maintenance window execution Application & Role Awareness Experience upgrading servers with common roles such as: Active Directory Domain Services (non‑FSMO or with coordination)

DNS / DHCP IIS

File & Print Services SQL Server (OS upgrade support validation) Ability to identify workloads not suited for in‑place upgrade and recommend alternatives Security & Compliance Considerations Understanding of TLS, cipher, and security baseline changes between Server 2016 and newer versions Ability to validate: Antivirus / EDR compatibility post‑upgrade GPO and local policy behavior after upgrade