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AI Can Write a Better Phishing Email Than You. Here’s Why That Should Terrify You

AI Can Write a Better Phishing Email Than You. Here’s Why That Should Terrify You

Update: 2025-06-28
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Sorry in advance for the wonk audio!!





AI is everywhere—and it's not just writing poems or generating cat pics. In this episode of Legitimate Cybersecurity, Frank Downs and Dustin Burr dive deep into the impact of artificial intelligence on the world of cybersecurity.





From the myth of Artificial General Intelligence (AGI) to AI-powered pentesting and blue team burnout, we demystify the buzzwords, talk real-world applications, and get a little weird with some philosophical takes. And yes, Clippy makes a comeback.





🧠 Topics Covered:





What AI really is (with NIST definitions)





Can AI replace cybersecurity professionals?





AI in offensive vs. defensive security





LLM hallucinations and real-world risks





Deepfakes, phishing, and governance tools





The rise of AI girlfriends 😬





🧪 Outrageous Statements Segment:


We say wild things. Sometimes they’re true. Sometimes they’re spicy. Always entertaining.





📍 Special shoutouts to:





Dr. Charles Harry (coming soon!)





Clippy (RIP king)





👂 Listen on Spotify, Apple, or wherever you get your podcasts.





👉 Like, Subscribe, and Share if you want to see Eeyore smile again.


#cybersecurity #artificialintelligence #pentesting


#podcast #Deepfakes #chatgpt #llm #infosec #aiincybersecurity #generativeai


#clippyisback





00:00 – Intro: Art, AI, and Losing Viewers


00:33 – The Hollywood AI Myth: Smart Computer = Death


02:25 – Breaking Down AI Fear and Misunderstanding


03:47 – What AI Actually Is (and Isn’t)


05:19 – Remembering Clippy: The First “AI Assistant”


06:20 – Demystifying AI Through NIST Definitions


08:45 – AI vs. Machine Learning: What’s the Difference?


11:18 – What is a Large Language Model (LLM)?


12:31 – Generative AI & Artificial General Intelligence (AGI)


13:56 – Can AGI Replace Humans? A Futurist’s Perspective


16:00 – AI's Limits: Empathy, Reasoning, and Hallucinations


18:09 – Should AI Do the Menial Work While Humans Create?


19:03 – AI as Friend, Lover, and Therapist: A Cultural Shift


21:00 – The Danger of Replacing Human Connection


22:36 – AI Marriages and Japan's Pillow Brides


24:00 – AI Partners = Modern Incel Cat Ladies?


25:00 – Satire, Safety, and Securing Your AI Spouse


26:31 – Why AI Still Can’t Replace Real Human Emotion


27:19 – Hollywood’s Obsession With AI Relationships


29:03 – Don’t Replace Human Connection With Anything


29:31 – AI in Offensive Cybersecurity & Pen Testing


31:33 – AI-Powered Pentests: Regulation vs. Automation


33:13 – Exploit Development, Intuition & Quantum Chaos


34:45 – Use AI to Handle the Mundane, Focus on the Critical


36:03 – Deepfakes, CEO Scams & Social Engineering


37:23 – AI + Polymorphic Code = Scary Smart Attacks


38:55 – AI for Blue Teams: Helping Analysts, Not Replacing Them


41:21 – AI in Governance: From Policy Writing to NIST Alignment


43:11 – Academic Uses: Research, Summaries, & Cleanups


45:40 – What’s Coming: Academic Deep Dive Next Week


47:06 – Staying Relevant: Experiment, Learn, and Evolve


48:57 – AI as a Communication Tool in Cybersecurity


50:21 – NEW SEGMENT – Outrageous Statements Begins!


51:01 – AI Writes Better Phishing Emails?


51:23 – Will AI Replace SOC Analysts?


52:51 – Can You Use AI to Build a Risk Register?


54:31 – Mickey, MidJourney, and Deepfake Ethics


55:31 – AI Hallucinations Will Cause Real Incidents

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AI Can Write a Better Phishing Email Than You. Here’s Why That Should Terrify You

AI Can Write a Better Phishing Email Than You. Here’s Why That Should Terrify You

LegitimateCybersecurity