Windows Server Upgrade Analyst

Client: Utilities CompanyPosition: Windows Server Upgrade AnalystTerm: 1 year Contract - May 2026 - April 2027Pay: $53/Hr - 56/Hr Location: Tampa, FLWork 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 2022Strong understanding of Windows Server upgrade paths, edition compatibility, and licensing implicationsAbility to assess and remediate pre‑upgrade blockers (deprecated roles, drivers, legacy applications)Hands‑on experience reviewing and resolving setupact.log / setuperr.log issuesKnowledge of supported .NET, PowerShell, and role dependencies across Windows Server versionsExperience validating post‑upgrade OS health (services, roles, performance, event logs)VMware vSphere & Virtual Machine Operations:Experience working with VMware vSphere / ESXi virtual machinesVM snapshots (pre‑upgrade and rollback planning)Disk space checks and expansion if requiredVMware Tools verification and upgradesUnderstanding of vCPU, memory, and virtual hardware compatibility with newer Windows Server versionsPre‑Upgrade Planning & Risk Mitigation:Run and interpret Windows Upgrade Readiness checksVerify application and vendor support for target OSConfirm backup validity and recovery optionsSecurity & Compliance Considerations:Understanding of TLS, cipher, and security baseline changes between Server 2016 and newer versionsAntivirus / EDR compatibility post‑upgradeGPO and local policy behavior after upgrade