Windows Patching, Automation Engineer

This is a fully remote position, open to applicants in Latin America.

📋 Description

• Develop, maintain, and troubleshoot PowerShell scripts for patch deployment, diagnostics, remediation, and reporting.

• Assist with monthly Windows security patch rollouts, which include official and prerelease updates, antivirus updates, .NET updates, and associated security and compliance components.

• Investigate Windows Update and MSU installation failures by analyzing Windows event logs, CBS logs, installer logs, and error codes.

• Examine logs and telemetry across different systems to identify failure patterns, technical obstacles, and necessary remediation steps.

• Utilize KQL to analyze deployment results, oversee patch and vulnerability compliance, and pinpoint systems that need follow-up actions.

• Confirm installed Windows updates, packages, operating system versions, and runtime versions.

• Create, validate, and distribute patching components and packages across deployment rings and environments.

• Address issues related to machine state, network connectivity, capacity, installation failures, and environment-specific conditions.

• Maintain dashboards, monitoring tools, compliance reports, and investigation documentation.

• Collaborate with partner teams to resolve exceptions, manual interventions, and technical issues, escalating problems with diagnostic evidence.

• Provide support for a client engagement anticipated to last for 18 months.

⛳️ Requirements

• Practical experience with PowerShell scripting and automation, including the ability to write, modify, and debug scripts.

• Knowledge of PowerShell’s object-based pipeline and filtering methods, such as Where-Object.

• Strong debugging and troubleshooting skills across various systems using logs and telemetry.

• Familiarity with Windows Update, Windows Server Update Services (WSUS), and manual MSU installation.

• Experience in troubleshooting Windows update or package installation failures by using event logs, servicing or installer logs, and error-code analysis.

• Capability to verify installed Windows updates and packages through Get-HotFix, Get-WindowsPackage, DISM, or Windows Update history.

• Hands-on experience with KQL to query and analyze operational data in Kusto.

• Excellent communication skills and the ability to document findings clearly while collaborating with engineering, security, and compliance teams.

• Preferred: experience in supporting patching or vulnerability compliance in a large, distributed Windows server environment.

• Preferred: experience with Azure DevOps build or deployment pipelines.

• Preferred: familiarity with .NET servicing and identifying installed .NET runtimes.

• Preferred: knowledge of antivirus servicing and vulnerability scanning tools.

• Preferred: experience linking CVEs to patching or vulnerability remediation efforts.

• Preferred: familiarity with deployment rings, safe deployment practices, Windows hotpatching, operating system baselines, STIGs, or WinPE.

🏝️ Benefits

• Medical, dental, and vision coverage.

• Flexible Spending Account (FSA).

• 401(k) retirement plan.

• Competitive paid time off.

• Parental leave.

• Opportunities for professional growth and development.

• Benefits, statutory entitlements, and any additional required payments comply with applicable local employment regulations.