Our Victoria area client is a leader in the support and provision of healthcare services to the British Columbia public. The client is seeking a Specialist Technical Analyst on a remote, contract basis to support activities within IT Infrastructure Solutions & Services. Project Description: The client organization is undertaking a 12-month infrastructure modernization initiative focused on remediating 500 legacy Windows 2016 Servers, preparing Windows Server 2025 for use in production, improving management and deployment of Windows servers through automation. The client requires one expert-level technical resource to provide hands-on infrastructure modernization services, including server lifecycle upgrades, automation implementation, and monitoring improvements. Objectives The primary objectives of this engagement are: - Remediate legacy Windows Server 2016 environments.
- Validate and standardize Windows Server 2025 deployments.
- Implement infrastructure automation using Ansible and other tools.
- Establish Azure Arc-based on premise patch automation.
Improve monitoring coverage across Windows and RHEL environments using Control up and Azure Arc. Anticipated services include: Scope of Services The Contractor will work under the direction of technical leads and subject matter experts to support day-to-day infrastructure modernization activities and operational implementation requirements. Island Health will provide overall direction, priorities, and oversight for the work. The Contractor will provide technical services across the following priority areas. Priority 1: Legacy Server Upgrades The Contractor will: - Perform in-place and side-by-side upgrades of Windows Server 2016 to Windows Server 2022 and/or 2025.
- Support VMware ESXi virtual machines and physical “bare metal” servers.
- Coordinate with project managers and server/application owners to:
- Conduct service discovery
- Validate compatibility
- Execute upgrade plans
- Perform post-upgrade validation and troubleshooting
Deliverables: - Upgrade servers as required.
- Post-upgrade validation reports.
- Updated configuration documentation.
Priority 2: Windows Server 2025 Validation & Hardening The Contractor will: - Produce prepare Windows Server 2025 for use in production, and verify compatibility with:
- VMware ESXi infrastructure
- Security tooling (e.g., CrowdStrike)
- Monitoring tools (ControlUP, SCOM)
- Configuration management (SCCM)
- Develop a hardened Windows Server 2025 baseline configuration, stripping all non-essential Microsoft default components
- Build a hardened deployment of Windows Server 2025, stripping all non-essential Microsoft default components.
- Provide hardening templates as Ansible playbooks, scripts, or VMware templates to ensure long-term maintainability.
Deliverables: - Server 2025 prepared and ready for production use and deployment
- Provide documentation on server hardening and configuration.
- Automation artifacts (playbooks/templates)
- Final gold image/templates made available to operations team for additional deployments
Priority 3: Azure Arc Integration & Patch Automation (As Time Permits) The Contractor will: - Develop documentation to support an Architecture Review Board (ARB) submission for Azure Arc usage for patching and compliance reporting, addressing:
- Security
- Privacy
- Network requirements
- Cost implications
- Design and implement onboarding of on-premises servers into Azure Arc for patching and compliance reporting.
- Configure resource tagging aligned with landing zone standards.
- Implement Azure Update Manager to replace legacy patching methods with automated schedules and real-time compliance reporting.
Deliverables: - ARB-ready technical documentation
- Azure Arc onboarding framework
- Automated patch schedule configuration and deployment to Windows Server fleet.
- Compliance reporting dashboard
Priority 4: Infrastructure Automation Framework (As Time Permits) The Contractor will: - Implement Ansible as the primary automation engine for server provisioning and configuration.
- Develop a standardized “push-button” Windows Server 2025 deployment workflow.
- Ensure automated tagging and monitoring registration during build.
Deliverables: - Infrastructure automation design documentation
- Reusable Ansible playbooks
- Deployment workflow documentation
- Knowledge transfer session(s)
Priority 5 – Hybrid Monitoring Improvements (As Time Permits) The Contractor will: - Implement Azure Monitor/Log Analytics as a Proof of Concept (POC) to fill telemetry gaps that ControlUP cannot address.
- Define a strict ingestion scope to prevent ballooning costs in Log Analytics, focusing on “free” tier data where possible.
- Develop custom workbooks to monitor OS health and service availability across Windows and RHEL.
Deliverables: - Monitoring POC deployment
- Ingestion policy documentation
- Custom monitoring dashboards/workbooks
- Cost monitoring strategy
Maximum number of candidate submissions: 1 Note that due to cost and logistics factors, our client has a preference for candidates residing local to this opportunity. If suitable please apply today! There is an excellent chance of extension. Deadline is May 31, 2026. | 