Windows Patching & Automation Engineer

Role overview Help maintain security and vulnerability compliance across a large, distributed Windows server environment. You’ll support regular patching and related software updates, automate deployment and reporting tasks, and investigate failures using logs, telemetry, and deployment data. The role involves coordinating with engineering, security, and compliance teams to resolve technical blockers and verify that updates are installed safely.

Responsibilities - Write, maintain, and debug PowerShell scripts for patch deployment, diagnostics, remediation, and reporting. - Support monthly Windows security, antivirus, and .NET updates, including prerelease updates where applicable. - Investigate Windows Update and MSU installation failures using event, servicing, and installer logs and error codes. - Query deployment results with Kusto Query Language (KQL), monitor compliance, and identify systems that need follow-up. - Verify installed updates, packages, operating system versions, and runtimes; maintain dashboards and investigation notes. - Build and publish patching packages using safe deployment practices, and coordinate resolutions for exceptions and environment-specific blockers.

Requirements - Hands-on experience writing, modifying, and debugging PowerShell scripts, including use of its object pipeline and filtering methods. - Working knowledge of Windows Update, WSUS, and manual MSU installation. - Experience troubleshooting update or package installation problems with logs and error codes. - Ability to verify updates and packages using tools such as Get-HotFix, Get-WindowsPackage, DISM, or Windows Update history. - Practical experience querying operational data with KQL. - Clear technical documentation and communication with engineering, security, and compliance partners.

Nice to have Experience with large-scale Windows patching, Azure DevOps pipelines, .NET or antivirus servicing, vulnerability scanning, CVE remediation, deployment rings, Windows hotpatching, baselines, STIGs, or WinPE.

Benefits and work setup Remote role for candidates based in Latin America, with an expected 18-month client engagement and local employment through a PEO or employer-of-record partner. Estimated pay is $2,200–$2,500 USD per month, subject to location, experience, and internal equity; it may be paid in local currency. Eligible benefits may include medical, dental and vision coverage, an FSA, retirement plan, paid time off, parental leave, and professional development; availability varies by location and employment status.