Windows Server Upgrade Engineer

We are seeking an experienced Windows Server Upgrade Engineer to lead and execute an enterprise-wide upgrade of Windows Server 2016 to Windows Server 2022 or 2025.The ideal candidate will have strong hands‑on expertise in server administration, automated provisioning, patching, GPO management, and troubleshooting complex infrastructure issues.Key ResponsibilitiesPlan, execute, and document the end-to-end Windows Server upgrade process (2016 → 2022/2025).Perform pre‑migration assessments, compatibility checks, and remediation activities.Provision new servers using automated deployment technologies.Implement and oversee patching cycles via SCCM, Azure Update Manager, or similar platforms.Coordinate with application SMEs to plan and communicate application downtime, ensuring minimal business impact during upgrade windows.Troubleshoot OS‑level and SQL/Windows Cluster issues, AD domain interactions, GPO conflicts, network dependencies, and application compatibility problems.Collaborate with security and application teams to ensure compliance and smooth cutover.Maintain accurate documentation, upgrade runbooks, rollback steps, and test validations.Ensure minimal downtime and strict adherence to change management processes.Required Skills & Experience5+ years of hands‑on experience in Windows Server administration (2012/2016/2019/2022).Proven experience upgrading or migrating Windows Server environments.Strong understanding of Active Directory, DNS, DHCP, Failover Clustering, and GPOs.Experience with automated server provisioning (PowerShell DSC, SCCM, Azure Automation, Terraform/Ansible optional).Deep knowledge of patching tools (SCCM, Azure Update Manager) and experience managing VMware vCenter environments.Strong PowerShell scripting skills for automation and troubleshooting.Familiarity with virtualization platforms (VMware) with strong ESXi‑specific administration and troubleshooting experience.Ability to diagnose performance issues using OS‑level and network‑level tools.Experience in enterprise change‑control and documentation practices.Preferred QualificationsMicrosoft Certified: Windows Server Hybrid Administrator Associate (or similar).Experience with parallel or in‑place upgrade strategies.Exposure to cloud‑integrated Windows Server workloads (Azure AD Connect, hybrid joins).Soft SkillsExcellent coordination and communication skills, especially when working with application SMEs and business stakeholders.Ability to work under pressure during maintenance windows.Strong problem‑solving capability and ownership mindset.#J-18808-Ljbffr