We present an end-to-end demonstration of how attackers can exploit AI safety failures to harm vulnerable populations: from jailbreaking LLMs to generate phishing content, to deploying those messages against real targets, to successfully compromising elderly victims. We systematically evaluated safety guardrails across six frontier LLMs spanning four attack categories, revealing critical failures where several models exhibited near-complete susceptibility to certain attack vectors. In a human validation study with 108 senior volunteers, AI-generated phishing emails successfully compromised 11\% of participants. Our work uniquely demonstrates the complete attack pipeline targeting elderly populations, highlighting that current AI safety measures fail to protect those most vulnerable to fraud. Beyond generating phishing content, LLMs enable attackers to overcome language barriers and conduct multi-turn trust-building conversations at scale, fundamentally transforming fraud economics. While some providers report voluntary counter-abuse efforts, we argue these remain insufficient.