Windows Server Upgrade Analyst
The Value Maximizer, Florida, NY, United States
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 & Qualifications
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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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 & Qualifications
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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