Windows Server Upgrade Engineer/Admin

Lutz, FL, US • Posted 2 days ago • Updated 1 hour ago
Contract W2
12 Months
No Travel Required
On-site
Depends on Experience
Fitment

Dice Job Match Score™

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Job Details

Skills

  • VMware ESXi
  • Microsoft Windows
  • VMware vSphere
  • Windows PowerShell
  • Virtual Machines
  • Servers
  • Microsoft Windows Server
  • Active Directory
  • Server Upgrade

Summary

Core Windows Server Upgrade Skills

  • Proven experience performing inplace upgrades from Windows Server 2016 to 2019 and/or 2022
  • Strong understanding of Windows Server upgrade paths, edition compatibility, and licensing implications
  • Ability to assess and remediate preupgrade blockers (deprecated roles, drivers, legacy applications)
  • Handson experience reviewing and resolving setupact.log / setuperr.log issues
  • Knowledge of supported .NET, PowerShell, and role dependencies across Windows Server versions
  • Experience validating postupgrade OS health (services, roles, performance, event logs)

VMware vSphere & Virtual Machine Operations

  • Experience working with VMware vSphere / ESXi virtual machines
  • Ability to safely perform:
    • VM snapshots (preupgrade and rollback planning)
    • Disk space checks and expansion if required
    • VMware Tools verification and upgrades
  • Understanding of vCPU, memory, and virtual hardware compatibility with newer Windows Server versions

PreUpgrade Planning & Risk Mitigation

  • Ability to:
    • Run and interpret Windows Upgrade Readiness checks
    • Verify application and vendor support for target OS
    • Confirm backup validity and recovery options
  • Experience documenting:
    • Upgrade plans
    • Rollback procedures
    • Success criteria and validation steps
  • Familiarity with change management and maintenance window execution

Application & Role Awareness

  • Experience upgrading servers with common roles such as:
    • Active Directory Domain Services (nonFSMO or with coordination)
    • DNS / DHCP
    • IIS
    • File & Print Services
    • SQL Server (OS upgrade support validation)
  • Ability to identify workloads not suited for inplace upgrade and recommend alternatives

Security & Compliance Considerations

  • Understanding of TLS, cipher, and security baseline changes between Server 2016 and newer versions
  • Ability to validate:
    • Antivirus / EDR compatibility postupgrade
    • GPO and local policy behavior after upgrade
Employers have access to artificial intelligence language tools (“AI”) that help generate and enhance job descriptions and AI may have been used to create this description. The position description has been reviewed for accuracy and Dice believes it to correctly reflect the job opportunity.
  • Dice Id: apn
  • Position Id: Windows_STECO
  • Posted 2 days ago
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