Windows Server Upgrade Analyst

Qode • Florida, FL

2d • $53 - $56

About The Position

This position is responsible for performing in‑place upgrades from Windows Server 2016 to 2019 and/or 2022

Requirements

• 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)
• Experience working with VMware vSphere / ESXi virtual machines
• 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
• Run and interpret Windows Upgrade Readiness checks
• Verify application and vendor support for target OS
• Confirm backup validity and recovery options
• Understanding of TLS, cipher, and security baseline changes between Server 2016 and newer versions
• Antivirus / EDR compatibility post‑upgrade
• GPO and local policy behavior after upgrade

Responsibilities

• Performing in‑place upgrades from Windows Server 2016 to 2019 and/or 2022
• Assess and remediate pre‑upgrade blockers (deprecated roles, drivers, legacy applications)
• Reviewing and resolving setupact.log / setuperr.log issues
• Validating post‑upgrade OS health (services, roles, performance, event logs)
• VM snapshots (pre‑upgrade and rollback planning)
• Disk space checks and expansion if required
• VMware Tools verification and upgrades
• Run and interpret Windows Upgrade Readiness checks
• Verify application and vendor support for target OS
• Confirm backup validity and recovery options

What This Job Offers

• Career Level: Mid Level
• Education Level: No Education Listed