Lateral Phishing With Large Language Models: A Large Organization Comparative Study
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Abstract (arXiv)
The emergence of Large Language Models (LLMs) has heightened the threat of phishing emails by enabling the generation of highly targeted, personalized, and automated attacks. Traditionally, many phishing emails have been characterized by typos, errors, and poor language. These errors can be mitigated by LLMs, potentially lowering the barrier for attackers. Despite this, there is a lack of large-scale studies comparing the effectiveness of LLM-generated lateral phishing emails to those crafted by humans. Current literature does not adequately address the comparative effectiveness of LLM and human-generated lateral phishing emails in a real-world, large-scale organizational setting, especially considering the potential for LLMs to generate more convincing and error-free phishing content. To address this gap, we conducted a pioneering study within a large university, targeting its workforce of approximately 9,000 individuals including faculty, staff, administrators, and student workers. Our results indicate that LLM-generated lateral phishing emails are as effective as those written by communications professionals, emphasizing the critical threat posed by LLMs in leading phishing campaigns. We break down the results of the overall phishing experiment, comparing vulnerability between departments and job roles. Furthermore, to gather qualitative data, we administered a detailed questionnaire, revealing insights into the reasons and motivations behind vulnerable employee's actions. This study contributes to the understanding of cyber security threats in educational institutions and provides a comprehensive comparison of LLM and human-generated phishing emails' effectiveness, considering the potential for LLMs to generate more convincing content. The findings highlight the need for enhanced user education and system defenses to mitigate the growing threat of AI-powered phishing attacks.
Key facts. Cited by 12 papers in the map (data through 7 Oct 2026). Builds on 11 of its 71 references that are in the map. First posted on arXiv 18 Jan 2024.
Builds on
11 of 71 references.
References · 11
- 2023DetectGPT: Zero-Shot Machine-Generated Text Detection using Probability Curvaturecited by 705
- 2023The Science of Detecting LLM-Generated Textscited by 126
- 2023Spear Phishing With Large Language Modelscited by 49
- 2023Digital Deception: Generative Artificial Intelligence in Social Engineering and Phishingcited by 26
- 2019Detecting and Characterizing Lateral Phishing at Scalecited by 20
- 2023The Looming Threat of Fake and LLM-generated LinkedIn Profiles: Challenges and Opportunities for Detection and Preventioncited by 18
- 2019SOK: A Comprehensive Reexamination of Phishing Research from the Security Perspectivecited by 15
- 2023From Chatbots to PhishBots? -- Preventing Phishing scams created using ChatGPT, Google Bard and Claudecited by 12
- 2024Deciphering Textual Authenticity: A Generalized Strategy through the Lens of Large Language Semantics for Detecting Human vs. Machine-Generated Textcited by 5
- 2021Phishing in Organizations: Findings from a Large-Scale and Long-Term Studycited by 4
- 2023Risk-Based Authentication for OpenStack: A Fully Functional Implementation and Guiding Examplecited by 1
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Citing papers per year: 2024: 6; 2025: 3; 2026: 3.
12 papers.
- 2024CYBERSECEVAL 3: Advancing the Evaluation of Cybersecurity Risks and Capabilities in Large Language Modelscited by 56
- 2024KnowPhish: Large Language Models Meet Multimodal Knowledge Graphs for Enhancing Reference-Based Phishing Detectioncited by 29
- 2025Jailbreak Attack Initializations as Extractors of Compliance Directionscited by 10
- 2024TrustAI at SemEval-2024 Task 8: A Comprehensive Analysis of Multi-domain Machine Generated Text Detection Techniquescited by 3
- 2024Assessing AI-Generated vs. Human-Authored Spear Phishing SMS Attacks: An Empirical Studycited by 1
- 2024Psychological Profiling in Cybersecurity: A Look at LLMs and Psycholinguistic Featurescited by 1
- 2025Generative AI for Internet of Things Security: Challenges and Opportunitiescited by 1
- 2025PiMRef: Deducing Ever-evolving Spear-phishing Emails with Knowledge Base Invariantscited by 1
- 2024Navigating the Knowledge Sea: Planet-scale answer retrieval using LLMscited by 0
- 2026Can LLM Agents Simulate Dynamic Networks? A Case Study on Email Networks with Phishing Synthesiscited by 0
- 2026Adversarial Robustness of Phishing Email Detection: A Comparative Study of TF-IDF + Logistic Regression and Fine-Tuned DistilBERTcited by 0
- 2026Beyond Detection: Evaluating Defensive LLMs Against AI-Generated Social Engineering in Live Turn-by-Turn Interactioncited by 0
- 2026Beyond Detection: Evaluating Defensive LLMs Against AI-Generated Social Engineering in Live Turn-by-Turn Interaction10 Aug 2026
- 2026Adversarial Robustness of Phishing Email Detection: A Comparative Study of TF-IDF + Logistic Regression and Fine-Tuned DistilBERT20 Jul 2026
- 2026Can LLM Agents Simulate Dynamic Networks? A Case Study on Email Networks with Phishing Synthesis20 Mar 2026
- 2025PiMRef: Deducing Ever-evolving Spear-phishing Emails with Knowledge Base Invariants21 Jul 2025
- 2025Jailbreak Attack Initializations as Extractors of Compliance Directions13 Feb 2025
- 2025Generative AI for Internet of Things Security: Challenges and Opportunities13 Feb 2025
- 2024CYBERSECEVAL 3: Advancing the Evaluation of Cybersecurity Risks and Capabilities in Large Language Models2 Aug 2024
- 2024Psychological Profiling in Cybersecurity: A Look at LLMs and Psycholinguistic Features26 Jun 2024
- 2024Assessing AI-Generated vs. Human-Authored Spear Phishing SMS Attacks: An Empirical Study18 Jun 2024
- 2024TrustAI at SemEval-2024 Task 8: A Comprehensive Analysis of Multi-domain Machine Generated Text Detection Techniques25 Mar 2024
- 2024KnowPhish: Large Language Models Meet Multimodal Knowledge Graphs for Enhancing Reference-Based Phishing Detection4 Mar 2024
- 2024Navigating the Knowledge Sea: Planet-scale answer retrieval using LLMs7 Feb 2024