Position Details

Salary $53 – $53 USD / year

Type Contract

Experience mid

Exp. Years Not specified

Education Not specified

Category System Administration

About this role

This role performs in-place upgrades of Windows Server from 2016 to 2019 and/or 2022 for a Utilities Company in Tampa, FL. The analyst will plan upgrades, troubleshoot readiness and setup logs, manage VMware virtual machine considerations, and verify post-upgrade health.

Key Responsibilities

Perform in-place upgrades from Windows Server 2016 to 2019 and/or 2022
Assess and remediate pre-upgrade blockers (deprecated roles, drivers, legacy applications)
Review and resolve setupact.log / setuperr.log issues
Validate post-upgrade OS health (services, roles, performance, event logs)
Plan and manage VMware vSphere/ESXi upgrade considerations (snapshots, disk space, VMware Tools, compatibility)

Technical Overview

You will execute Windows Server in-place upgrades across specific OS versions, ensuring upgrade paths, edition compatibility, and licensing implications are handled correctly. You will use PowerShell and knowledge of .NET and role dependencies, review setupact.log/setuperr.log, and validate services/roles/performance/event logs after upgrade, while coordinating VMware vSphere/ESXi snapshot and VMware Tools readiness.

Ideal Candidate

The ideal candidate is a hands-on Windows systems administrator with proven experience performing in-place upgrades from Windows Server 2016 to 2019 and/or 2022. They can troubleshoot upgrade blockers using setupact.log and setuperr.log, validate post-upgrade OS health, and manage VMware vSphere/ESXi virtual machine considerations including snapshots and VMware Tools.

Must-Have Skills

Proven experience performing in-place upgrades from Windows Server 2016 to 2019 and/or 2022Strong understanding of Windows Server upgrade pathsedition compatibilityand licensing implicationsAbility to assess and remediate pre-upgrade blockers (deprecated rolesdriverslegacy applications)Hands-on experience reviewing and resolving setupact.log / setuperr.log issues

Tools & Platforms

Windows Server 2016Windows Server 2019Windows Server 2022setupact.logsetuperr.logPowerShellVMware vSphereVMware ESXiVM snapshotsVMware ToolsGPO

Required Skills

Windows Server 2016Windows Server 2019Windows Server 2022in-place upgradesWindows Server upgrade pathsedition compatibilitylicensing implicationsdeprecated rolesdriverslegacy applicationssetupact.logsetuperr.log.NETPowerShellrole dependenciesOS health validationevent logsVMware vSphereVMware ESXiVM snapshotsVMware ToolsvCPUvirtual hardware compatibilityWindows Upgrade Readiness checksTLSAntivirusEDR compatibilityGPOlocal policy behavior

Hard Skills

Windows ServerWindows Server 2016Windows Server 2019Windows Server 2022in-place upgradesWindows Server upgrade pathsedition compatibilitylicensing implicationsdeprecated rolesdriverslegacy applicationssetupact.logsetuperr.log.NETPowerShellrole dependenciesOS health validationservicesrolesperformanceevent logsVMware vSphereVMware ESXivirtual machine snapshotspre-upgrade and rollback planningdisk space checksdisk expansionVMware Tools verificationVMware Tools upgradesvCPUvirtual hardware compatibilityWindows Upgrade Readiness checksapplication supportvendor support for target OSbackup validityrecovery optionsTLSciphersecurity baseline changesAntivirusEDR compatibilityGPO and local policy behaviorGPO

Soft Skills

analyzing and assessing pre-upgrade blockersproblem-solvingattention to detailreporting

Industry & Role

Industry Government/Public Sector

Job Function Perform and troubleshoot Windows Server in-place upgrades with VMware vSphere/ESXi support and post-upgrade validation.

Role Subtype Windows Sysadmin

Tech Domains Windows Server, VMware, Networking / TCP-IP, Cybersecurity, Power BI

Clearance & Visa

Visa Sponsorship No

Keywords for Your Resume

Windows Server Upgrade AnalystWindows Server 2016Windows Server 2019Windows Server 2022in-place upgradesWindows Server upgrade pathsedition compatibilitylicensing implicationssetupact.logsetuperr.log.NETPowerShellVMware vSphereVMware ESXiVM snapshotsVMware ToolsWindows Upgrade Readiness checksTLSEDR compatibilityGPOlocal policyevent logs

Deal Breakers

Must have proven experience performing in-place upgrades from Windows Server 2016 to 2019 and/or 2022, Must have hands-on experience reviewing and resolving setupact.log / setuperr.log issues, Must be authorized to work in the US as USC or GC ONLY, Must be able to work on-site in Tampa, FL

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