Window Server Upgrade

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.

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