Windows Server Upgrade Analyst

Qode

Florida, Florida, United States contract

Posted: April 13, 2026

Required Skills

Job Description

Client: Utilities Company
Position: Windows Server Upgrade Analyst
Term: 1 year Contract - May 2026 - April 2027
Pay: $53/Hr - 56/Hr
Location: Tampa, FL
Work Authorization: USC or GC ONLY

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

Experience:
• 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
• 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:
• Run and interpret Windows Upgrade Readiness checks
• Verify application and vendor support for target OS
• Confirm backup validity and recovery options
• Security & Compliance Considerations:
• 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

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