Windows Server Upgrade Analyst
Location: Florida, Florida, United States
Workplace: on_site
Employment Type: contract
Description
- 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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