Window Server Upgrade Engineer
$60 per hourLeading Utilities Organization
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
Vacancy posted 17 hours ago
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