compLogoWindows Server Upgrade AnalystCompany: Utilities CompanyOn-siteTampa, FL, USA
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