Windows Server Upgrade Engineer: VMware & Enterprise Infra

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 solutionscy> 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 #J-18808-Ljbffr Strategic Staffing Solutions