Top 5873 Windows Server Engineer Jobs

Windows Server Upgrade Engineer
Strategic Staffing Solutions —Lutz, FL
- $60 an hour
- Full-time
- Mid-level
- Windows
- High school diploma or GED
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11d
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Automation Systems Support Engineer
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PlayStation Global —Playa Vista, CA
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Select Minds LLC —Dallas, TX
- $55 - $65 an hour
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Cellebrite —Remote
- Full-time
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Airship —Remote
- $75,000 - $90,000 a year
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- Background check
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- Paid holidays

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Windows Server Upgrade Engineer

Strategic Staffing Solutions -
Lutz, FL

Quick Apply

Job Details

Full-time | Contract
$60 an hour

Qualifications

IIS
IT operations
Windows
High school diploma or GED
DHCP
DNS
Server virtualization
Windows support
PowerShell
ESXi
Active Directory management
Production troubleshooting

Full 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

Pay: $60.00 per hour

Work Location: In person

Quick Apply

Refine Your Search

Windows Server Engineer jobs

Windows Server Upgrade Engineer

Call Recording Speech Analytics Engineer

Senior Windows Server Engineer – Cloud Infrastructure

Server Engineer

IT Systems Engineer

Junior Developer

Assistant VP, Windows Server Engineer

Tier 3 Engineer

L3 Systems Engineer (Microsoft, Azure, Active Directory

Anticheat Software Engineer

Systems Engineer

Senior DevOps Engineer (Remote)

Application Support Engineer

Service Engineer

Automation Systems Support Engineer

Sr DevOps Engineer (Contract)

Systems Engineer

Senior Windows Engineer/Admin

Systems Engineer

IT Systems Engineer

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