Window Server Upgrade

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 / issues
• Knowledge of 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
• 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

Pre Upgrade 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 (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

Security & Compliance Considerations

• 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