Large Language Models (LLMs) are increasingly capable, aiding in tasks such as content generation, yet they also pose risks, particularly in generating harmful spear-phishing emails. These emails, crafted to entice clicks on malicious URLs, threaten personal information security. This paper proposes an adversarial framework, SpearBot, which utilizes LLMs to generate spear-phishing emails with various phishing strategies. Through specifically crafted jailbreak prompts, SpearBot circumvents security policies and introduces other LLM instances as critics. When a phishing email is identified by the critic, SpearBot refines the generated email based on the critique feedback until it can no longer be recognized as phishing, thereby enhancing its deceptive quality. To evaluate the effectiveness of SpearBot, we implement various machine-based defenders and assess how well the phishing emails generated could deceive them. Results show these emails often evade detection to a large extent, underscoring their deceptive quality. Additionally, human evaluations of the emails' readability and deception are conducted through questionnaires, confirming their convincing nature and the significant potential harm of the generated phishing emails.

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