Window Server Upgrade
Job Location:
Monthly Salary:
Posted on:
30+ days ago
Posted on:
Vacancies:
1 Vacancy
Vacancies:
Job Summary
REQUIRED 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 / 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:
o VM snapshots (pre upgrade and rollback planning)
o Disk space checks and expansion if required
o 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:
o Run and interpret Windows Upgrade Readiness checks
o Verify application and vendor support for target OS
o Confirm backup validity and recovery options
Experience documenting:
o Upgrade plans
o Rollback procedures
o Success criteria and validation steps
Familiarity with change management and maintenance window execution
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:
o VM snapshots (pre upgrade and rollback planning)
o Disk space checks and expansion if required
o 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:
o Run and interpret Windows Upgrade Readiness checks
o Verify application and vendor support for target OS
o Confirm backup validity and recovery options
Experience documenting:
o Upgrade plans
o Rollback procedures
o Success criteria and validation steps
Familiarity with change management and maintenance window execution
Application & Role Awareness
Experience upgrading servers with common roles such as:
o Active Directory Domain Services (non FSMO or with coordination)
o DNS / DHCP
o IIS
o File & Print Services
o SQL Server (OS upgrade support validation)
Ability to identify workloads not suited for in place upgrade and recommend alternatives
Experience upgrading servers with common roles such as:
o Active Directory Domain Services (non FSMO or with coordination)
o DNS / DHCP
o IIS
o File & Print Services
o 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:
o Antivirus / EDR compatibility post upgrade
o GPO and local policy behavior after upgrade
Understanding of TLS cipher and security baseline changes between Server 2016 and newer versions
Ability to validate:
o Antivirus / EDR compatibility post upgrade
o GPO and local policy behavior after upgrade
