Window Server Engineer
Role details
Job location
Tech stack
Requirements
- 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
- validating post upgrade OS health (services, roles, performance, event logs)
- VMware vSphere & Virtual Machine Operations
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Experience working with VMware vSphere / ESXi virtual machines
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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
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Understanding of vCPU, memory, and virtual hardware compatibility with newer Windows Server versions
- Pre Upgrade Planning & Risk Mitigation
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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
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Experience documenting:
- Upgrade plans
- Rollback procedures
- Success criteria and validation steps
- Familiarity with change management and maintenance window execution
- Application & Role Awareness
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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)
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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, * Highschool diploma and Experience required