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CHEESEHub is a web-accessible, public science gateway that hosts containerized, hands-on demonstrations of cybersecurity concepts. There are now a plethora of services and tools designed to simplify modern gateway deployment and configuration such as commercial and academic composable cloud, the Terraform infrastructure as service tool, Kubernetes and Helm for container orchestration, as well as CILogon for simplified user authentication. Despite leveraging these tools, our day-to-day experience with deploying, upgrading, scaling, and extending CHEESEHub has not been entirely straightforward. We describe here some of the major challenges we have encountered in managing CHEESEHub and developing web-accessible demonstrations for the last five years. We hope this will help both new and seasoned gateway developers to effectively leverage these modern tools while avoiding these same pitfalls, while also providing starting points for discussions about gateway development and deployment best-practices.