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Rupa Parameswaran, VP of Security & IT at Handshake, maps happy paths and documents every legitimate route for accessing, adding, moving, and removing crown jewels, then instruments alerts for everything outside those baselines. When AI tools get inadvertently connected to entire workspaces instead of individual accounts, these detection layers catch the exposure. Rupa details building lightweight apps that crawl vendor sites to flag consent changes, self-hosted deployment strategies that contain risk without reverting to bare metal, and why just-in-time access controls don't slow engineering velocity when implemented as the default path. Chapters: 00:00 Introduction 00:26 How Rupa got into security and privacy research 01:55 Privacy homomorphic encryption and data obfuscation 04:45 Building security programs: identifying crown jewels 06:06 The full spectrum of data security 06:52 Happy paths framework for detecting anomalies 08:44 Making security relevant to engineers focused on velocity 11:58 Third-party risk and AI vendor management 14:33 Top AI data protection and governance risks 18:08 Practical advice beyond pilots for scaling AI adoption 21:01 Self-hosted vs on-prem deployment strategies 22:26 Building effective security teams and cultural elements 24:22 Advice for security professionals starting out 25:47 Where to follow Rupa's work