Windows Server Upgrade Engineer

Job Description – Windows Server Upgrade Engineer (2016 → 2022/2025)

Position: Windows Server Upgrade Engineer

Department: Core-IT / Technology

Location: Abu Dhabi (On-site)

Contract Type: Project-based (1 yr)

Role Overview

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 Responsibilities

• Plan, 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 & Experience

• 5+ years 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 Qualifications

• Microsoft 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 Skills

• Excellent 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.