Windows Server Upgrade

$50 per hour

Temporary

Kforce has a client that is seeking a Window Server Upgrade (Mid-level 2-4 years) in Lutz, FL for an 8-month contract. Core Windows Server Upgrade Skills:

Proven experience performing in place 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 pre-upgrade blockers (deprecated roles, drivers, legacy applications)
Hands on experience reviewing and resolving setupact.log/setuperr.log issues
Knowledge of supported .NET, PowerShell, and role dependencies across Windows Server versions
Experience validating post upgrade 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 (pre upgrade 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

Pre Upgrade 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 (non FSMO or with coordination)

* DNS/DHCP

* IIS

File & Print Services
SQL Server (OS upgrade support validation)
Ability to identify workloads not suited for in place 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 post upgrade
GPO and local policy behavior after upgrade

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Vacancy posted 4 days ago

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