What are the responsibilities and job description for the Windows Server Upgrade Engineer/Admin position at Jobs via Dice?
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Core Windows Server Upgrade Skills
Core Windows Server Upgrade Skills
- 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)
- Experience working with VMware vSphere / ESXi virtual machines
- Ability to safely perform:
- 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
- Ability to:
- Run and interpret Windows Upgrade Readiness checks
- Verify application and vendor support for target OS
- Confirm backup validity and recovery options
- Experience documenting:
- Upgrade plans
- Rollback procedures
- Success criteria and validation steps
- Familiarity with change management and maintenance window execution
- Experience upgrading servers with common roles such as:
- Active Directory Domain Services (non‑FSMO or with coordination)
- DNS / DHCP
- IIS
- File & Print Services
- SQL Server (OS upgrade support validation)
- Ability to identify workloads not suited for in‑place upgrade and recommend alternatives
- Understanding of TLS, cipher, and security baseline changes between Server 2016 and newer versions
- Ability to validate:
- Antivirus / EDR compatibility post‑upgrade
- GPO and local policy behavior after upgrade