Window Server Engineer

Software Guidance & Assistance, Inc., (SGA), is searching for a Window Server Engineer for a contract assignment with one of our premier Utility services clients in Tampa, FL.

Responsibilities :

• 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
  • 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

Required Skills:

• Highschool diploma and Experience required

SGA is a technology and resource solutions provider driven to stand out. We are a women-owned business. Our mission: to solve big IT problems with a more personal, boutique approach. Each year, we match consultants like you to more than 1,000 engagements. When we say let's work better together, we mean it. You'll join a diverse team built on these core values: customer service, employee development, and quality and integrity in everything we do. Be yourself, love what you do and find your passion at work. Please find us at .

SGA is an Equal Opportunity Employer and does not discriminate on the basis of Race, Color, Sex, Sexual Orientation, Gender Identity, Religion, National Origin, Disability, Veteran Status, Age, Marital Status, Pregnancy, Genetic Information, or Other Legally Protected Status. We are committed to providing access, equal opportunity, and reasonable accommodation for individuals with disabilities in employment, and our services, programs, and activities. Please visit our company to request an accommodation or assistance regarding our policy

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