Abstract:This paper explores the rising concern of utilizing Large Language Models (LLMs) in spear phishing message generation, and their performance compared to human-authored counterparts. Our pilot study compares the effectiveness of smishing (SMS phishing) messages created by GPT-4 and human authors, which have been personalized to willing targets. The targets assessed the messages in a modified ranked-order experiment using a novel methodology we call TRAPD (Threshold Ranking Approach for Personalized Deception). Specifically, targets provide personal information (job title and location, hobby, item purchased online), spear smishing messages are created using this information by humans and GPT-4, targets are invited back to rank-order 12 messages from most to least convincing (and identify which they would click on), and then asked questions about why they ranked messages the way they did. They also guess which messages are created by an LLM and their reasoning. Results from 25 targets show that LLM-generated messages are most often perceived as more convincing than those authored by humans, with messages related to jobs being the most convincing. We characterize different criteria used when assessing the authenticity of messages including word choice, style, and personal relevance. Results also show that targets were unable to identify whether the messages was AI-generated or human-authored and struggled to identify criteria to use in order to make this distinction. This study aims to highlight the urgent need for further research and improved countermeasures against personalized AI-enabled social engineering attacks.