Search Jobs
Find the Position that's right for you.
So sorry, this position is no longer available.
Please go ahead and submit your application. We may have other positions that would be the perfect fit for you.
Alternatively, you may want to apply to one of the following related jobs:
Window Server Upgrade (802758)
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
Share This Job:
Related Jobs:
About Lutz, FL
Ready to discover exciting job opportunities in Lutz, Florida? Nestled in the heart of the Sunshine State, Lutz offers a perfect blend of picturesque landscapes, vibrant local culture, and a flourishing job market. With close proximity to Tampa and its renowned museums, theaters, and professional sports teams, as well as stunning nearby attractions like Hillsborough River State Park, Lutz is an ideal location for those seeking career growth and a high quality of life. Don't miss out on the chance to explore job listings in this charming and dynamic area – your dream career could be just around the corner!