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Design an ongoing AI red-team program: team, harm categories, cadence, and what you'd automate with PyRIT first.

The grown-up version of 'how would you red-team a chatbot', Microsoft-style loops ask for a program, not a pen test. Team composition, harm taxonomy, iteration cadence, and which attack classes you script on day one.

Updated Aug 2026 · Grounded in real Forward Deployed Engineer interview loops and written to a senior-engineer editorial bar.

The grown-up version of 'how would you red-team a chatbot', Microsoft-style loops ask for a program, not a pen test. Team composition, harm taxonomy, iteration cadence, and which attack classes you script on day one.

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