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Explore how to build secure agent fleet architectures that meet enterprise security requirements in this conference talk from the AI Engineer World's Fair. Learn about Gitpod's evolution from a self-hosted Kubernetes architecture to their current 'bring your own cloud' model that enables deployment of software engineering agent orchestration platforms in highly regulated environments. Discover the architectural decisions and security considerations necessary for scaling agent workloads in financial, insurance, and healthcare sectors where compliance and data protection are paramount. Examine the technical implementation of features like auto-suspend and resume capabilities for agent fleets, and understand how to securely integrate foundational models and agent memory solutions within enterprise constraints. Gain insights from years of practical experience in overcoming security blockers that prevent agent orchestration adoption in regulated industries, with specific focus on the challenges and solutions for deploying AI agents at scale while maintaining the security standards required by Chief Information Security Officers.