Job title: – Window Server Upgrade
Location: – Lutz, FL 33549
Duration: – 8 – 12-month contract
M – F 8 am – 5 pm M – F
Mid-Level 2-4 yrs.
Location: – Lutz, FL 33549
Duration: – 8 – 12-month contract
M – F 8 am – 5 pm M – F
Mid-Level 2-4 yrs.
Highschool diploma and Experience required
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)
- 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 behaviour after upgrade