Window Server Upgrade (802758)

Window Server Upgrade (802758) Lutz, FL 33549

Posted:

05/15/2026

Job Category:

Information Technology

Job Number:

56591967

Pay Rate:

$58.62 / hour Job Description Sirius Staffing is seeking a Windows Server Upgrade Specialist for a contract role in Lutz, Fl. We are seeking a Mid-Level Windows Server Upgrade Specialist to support enterprise server modernization efforts. This role focuses on performing in-place upgrades, validating system health, and ensuring secure and stable transitions across Windows Server environments within a virtualized VMware infrastructure. Key Responsibilities Windows Server Upgrades Perform in-place upgrades from Windows Server 2016 to 2019 and/or 2022 Identify and resolve pre-upgrade blockers such as deprecated roles, drivers, and legacy applications Review and troubleshoot upgrade logs (setupact.log, setuperr.log) Validate post-upgrade system health including services, roles, performance, and event logs Understand Windows Server upgrade paths, edition compatibility, and licensing considerations VMware & Virtual Infrastructure Work within VMware vSphere / ESXi environments Create and manage VM snapshots for upgrade rollback planning Perform disk space validation and expansion as needed Verify and upgrade VMware Tools Ensure virtual hardware compatibility with target Windows Server versions Upgrade Planning & Risk Mitigation Execute Windows Upgrade Readiness assessments Confirm application and vendor compatibility with target OS versions Validate backup integrity and recovery procedures Document upgrade plans, rollback strategies, and validation criteria Support change management processes and maintenance window execution Application & Server Roles Support upgrades involving: Active Directory Domain Services (non-FSMO roles or coordinated changes) DNS and DHCP IIS File and Print Services SQL Server (ensuring OS upgrade compatibility) Identify workloads unsuitable for in-place upgrades and recommend alternatives Security & Compliance Understand security changes between Windows Server 2016 and newer versions, including TLS and cipher updates Validate post-upgrade compatibility for: Antivirus / EDR solutions Group Policy Objects (GPOs) and local security policies Qualifications 2-4 years of relevant Windows Server administration or infrastructure experience Hands-on experience with Windows Server 2016/2019/2022 environments Strong VMware vSphere / ESXi experience Experience troubleshooting system logs and upgrade issues Familiarity with enterprise IT change management processes Strong attention to detail and documentation skills Meet Your Recruiter Bailee Stevens