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Explore the evolution of SSH honeypots and their role in DEF CON's Walkthrough Workshops through this 35-minute conference talk. Discover how an SSH honeypot puzzle at DEF CON 24 sparked the creation of the first Walkthrough Workshop at the Packet Hacking Village and learn about the ongoing influence of these interactive challenges. Examine Cowrie, a medium-interaction SSH honeypot, and understand how to enhance its capabilities beyond default settings through practical modifications. Delve into innovative implementations including custom commands, adventure games, and unique file system designs structured as spatial cubes. Gain insights into several years of Cowrie-based challenges that demonstrate creative approaches to terminal interaction and cybersecurity education. Understand the technical aspects of honeypot deployment and customization while exploring how these tools have been used to create engaging educational experiences in the cybersecurity community.