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I Built an AI That Tries to Phish Me Every Week — Here's What I Learned

DEV Community·晖丁·20 days ago
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The Problem I've been in security for about 5 years. I know what a phishing email looks like. I've given the trainings. I've written the policies. And yet, last week, I almost clicked a "Docusign invoice due" email at 4:30 PM on a Friday. In my own inbox. That moment made me realize: knowing about phishing and actually resisting phishing are two different skills. One is cognitive. The other is instinctual. The Solution: PhishGuard 🦞 So I built PhishGuard — a CLI tool that sends me one AI-generated phishing email every week. No calendar reminders, no heads-up. It just arrives. In my real inbox. Masquerading as a login alert, a package delivery notice, an HR policy update, a security warning.…

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