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Walks the four-paradigm evolution: rule-based (ELIZA pattern matching in 20 lines), retrieval-based (FAQ with similarity threshold), neural seq2seq (and why it loses solo), LLM agent loop (plan → tool → verify). Working demo: hybrid routing that sends destructive actions to structured flows, FAQs to retrieval, and ambiguous queries to an LLM agent fallback. This is the 2026 production pattern. Names five failure modes still shipping: confident fabrication, prompt injection, scope creep, infinite loops, context window exhaustion. Each with mitigation. Ship artifact: chatbot-architect skill that refuses pure-LLM agents for destructive actions without structured confirmation flows and requires prompt-injection audit for any write-access agent. ~75 minutes. Prerequisites lesson 05/13 and 05/14.