Build production-grade automation with Ansible and Python as a Senior Windows Server Automation Engineer in hybrid downtown Toronto. Work onsite two to three days weekly.One of Canada’s Big Five banks seeks a senior engineer for its Windows Engineering team. You will automate server lifecycles across physical and virtual environments using modular, idempotent, tested practices. The work includes Group Policy, security baselines, Active Directory, and infrastructure troubleshooting.Key Responsibilities:
Design reusable Ansible and Python server lifecycle automationApply source control, testing, logging,



and CI/CD practicesAutomate Group Policy security baselines and drift remediationResolve complex issues across infrastructure and security layersOwn technical designs and review production automation codeRequirements:
Eight-plus years supporting complex enterprise Windows Server environmentsHands-on Ansible or Python automation engineering experienceAdvanced Group Policy and Active Directory knowledgeExperience with clustering, Kerberos, certificates, patching, and remediationNetworking and performance tuning knowledge using stated toolsApply Windows Server expertise, Ansible or Python engineering, and security automation skills across enterprise infrastructure in Toronto.
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📌 Senior Windows Automation Engineer (Winnipeg)
🏢 Swoon
📍 Winnipeg