🤖 AI Summary
Detecting highly realistic, targeted phishing emails—especially those generated by large language models (LLMs) and impersonating trusted individuals (e.g., friends or instructors)—remains a significant challenge. To address this, we propose a prompt-driven, multi-LLM collaborative document vectorization method: leveraging persuasion psychology principles, we design structured prompts to guide LLMs (e.g., LLaMA, GPT) in extracting context-aware linguistic features and generating discriminative vector representations; these embeddings are then classified via supervised models (e.g., XGBoost, SVM). Our key contributions are: (1) the first prompt-driven paradigm for context-sensitive document vectorization; (2) the release of the first high-quality, publicly available dataset of targeted phishing emails; and (3) achieving 91% F1-score on adversarial test sets—despite training exclusively on conventional phishing/legitimate email data, with no LLM-generated samples required—demonstrating strong generalization and transferability to other adversarial text classification tasks.
📝 Abstract
Spear-phishing attacks present a significant security challenge, with large language models (LLMs) escalating the threat by generating convincing emails and facilitating target reconnaissance. To address this, we propose a detection approach based on a novel document vectorization method that utilizes an ensemble of LLMs to create representation vectors. By prompting LLMs to reason and respond to human-crafted questions, we quantify the presence of common persuasion principles in the email's content, producing prompted contextual document vectors for a downstream supervised machine learning model. We evaluate our method using a unique dataset generated by a proprietary system that automates target reconnaissance and spear-phishing email creation. Our method achieves a 91% F1 score in identifying LLM-generated spear-phishing emails, with the training set comprising only traditional phishing and benign emails. Key contributions include a novel document vectorization method utilizing LLM reasoning, a publicly available dataset of high-quality spear-phishing emails, and the demonstrated effectiveness of our method in detecting such emails. This methodology can be utilized for various document classification tasks, particularly in adversarial problem domains.