Job Description

Windows Server Upgrade Engineer

Location: Tampa, FL
Duration: 8–12 Month Contract
Pay Rate: $60/hr

Position Summary

We are seeking a Windows Server Upgrade Engineer to support enterprise infrastructure modernization initiatives in a VMware-based environment. This role will focus on performing in-place upgrades of Windows Server systems from 2016 to 2019/2022 while ensuring system stability, application compatibility, and successful post-upgrade validation.

The ideal candidate will have hands-on experience with Windows Server administration, VMware virtual machines, upgrade planning, troubleshooting, and production infrastructure support in an enterprise environment.

Key Responsibilities

• Perform in-place upgrades of Windows Server 2016 to Windows Server 2019 and/or 2022
• Assess and remediate upgrade blockers including deprecated roles, drivers, and legacy applications
• Review and troubleshoot upgrade logs including setupact.log and setuperr.log
• Validate server health, services, event logs, and application functionality after upgrades
• Create and manage VMware snapshots prior to upgrade activities
• Verify VMware Tools, virtual hardware compatibility, disk space, CPU, and memory requirements
• Execute upgrade readiness checks and support rollback planning as needed
• Coordinate maintenance windows and follow change management procedures
• Validate backup and recovery options prior to production changes
• Support Windows Server roles including:
  • Active Directory
  • DNS
  • DHCP
  • IIS
  • File & Print Services
• Review application compatibility and vendor support for target operating systems
• Ensure security and compliance standards remain intact following upgrades
• Validate antivirus, EDR, GPO, and policy functionality after upgrades
• Document upgrade plans, validation steps, rollback procedures, and outcomes

Required Qualifications

• High School Diploma or equivalent required
• 2–4+ years of Windows Server administration or infrastructure support experience
• Hands-on experience upgrading Windows Server environments
• Experience supporting VMware vSphere / ESXi virtual machines
• Strong troubleshooting and problem-solving skills
• Experience with Active Directory, DNS, DHCP, and IIS
• Familiarity with PowerShell and Windows administration tools
• Understanding of enterprise change management and maintenance window execution

Preferred Qualifications

• Experience supporting SQL Server environments during OS upgrades
• Knowledge of Windows Server licensing and upgrade compatibility
• Experience with enterprise backup and recovery solutions
• Understanding of security baseline changes between Windows Server versions
• Utility, enterprise operations, or large infrastructure environment experience preferred

Additional Information

• Candidates must be comfortable working in a production operations environment
• Strong communication and documentation skills are required
• This role is primarily focused on server infrastructure upgrades and operational stability