AI-generated phishing is getting terrifyingly good
We just caught a phishing campaign targeting our executives that was clearly AI-generated. Perfect grammar, personalized details scraped from LinkedIn, and the payload was a legit-looking DocuSign link.
The only reason we caught it: the sender domain was 2 days old. No SPF, no DKIM. But the content? Flawless.
How are you all training users for this new reality? Traditional "look for typos" advice is dead.
This is why we deployed Phishing? across all Outlook clients. The AI analysis catches domain age, header anomalies, and reputation signals that humans can't see. Users get a 0-100 score in 8 seconds instead of guessing.
We shifted our training from "spot the typo" to "verify the sender." We teach: 1) Check the actual From address, 2) Hover links before clicking, 3) When in doubt, report it. The Phishing? button makes step 3 instant.
The arms race is real. AI generates perfect phishing, AI detects it. The human layer is the weakest link. We're doing monthly simulated phishing now with increasing difficulty.
For executive protection, consider a dedicated communication channel. Our C-suite has a policy: any financial request over $5k must be confirmed via Signal or in-person. Saved us twice last quarter.
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