Window Server Upgrade
Title: Window Server Upgrade Location - Lutz, FL Shift Timing: Monday - Friday 8 AM -5 PM EST Duration: 8-12 month contract Highschool diploma and Experience required Complete Description: 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
