Windows Server Upgrade Engineer/Admin

Core Windows Server Upgrade Skills

• Proven experience performing inplace 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 preupgrade blockers (deprecated roles, drivers, legacy applications)
• Handson experience reviewing and resolving setupact.log / setuperr.log issues
• Knowledge of supported .NET, PowerShell, and role dependencies across Windows Server versions
• Experience validating postupgrade OS health (services, roles, performance, event logs)

VMware vSphere & Virtual Machine Operations

• Experience working with VMware vSphere / ESXi virtual machines
• Ability to safely perform:

• VM snapshots (preupgrade 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

PreUpgrade Planning & Risk Mitigation

• 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

Application & Role Awareness

• Experience upgrading servers with common roles such as:

• Active Directory Domain Services (nonFSMO or with coordination)
• DNS / DHCP
• IIS
• File & Print Services
• SQL Server (OS upgrade support validation)

• Ability to identify workloads not suited for inplace upgrade and recommend alternatives

Security & Compliance Considerations

• Understanding of TLS, cipher, and security baseline changes between Server 2016 and newer versions
• Ability to validate:

• Antivirus / EDR compatibility postupgrade
• GPO and local policy behavior after upgrade