# Detecting Jailbreak Attempts in Clinical Training LLMs Through Automated Linguistic Feature Extraction

arXiv: https://arxiv.org/abs/2602.13321 · HTML: https://mlsanity.com/paper/2602.13321/

## Key facts

- No citing papers in the map yet (data through 14 Oct 2026).
- Placed in Jailbreaking, one of 12 directions in LLM safety and security.
- Builds on 12 of its 15 references that are in the map.
- First posted on arXiv 10 Feb 2026.

## Placed in

- LLM safety and security / [Jailbreaking](https://mlsanity.com/safety/jailbreaking/)

## Builds on (most cited first, 12 of 12)

- [SmoothLLM: Defending Large Language Models Against Jailbreaking Attacks](https://mlsanity.com/paper/2310.03684/) (2023)
- [Detecting Language Model Attacks with Perplexity](https://mlsanity.com/paper/2308.14132/) (2023)
- [AutoDefense: Multi-Agent LLM Defense against Jailbreak Attacks](https://mlsanity.com/paper/2403.04783/) (2024)
- [GradSafe: Detecting Jailbreak Prompts for LLMs via Safety-Critical Gradient Analysis](https://mlsanity.com/paper/2402.13494/) (2024)
- [Gradient Cuff: Detecting Jailbreak Attacks on Large Language Models by Exploring Refusal Loss Landscapes](https://mlsanity.com/paper/2403.00867/) (2024)
- [JBShield: Defending Large Language Models from Jailbreak Attacks through Activated Concept Analysis and Manipulation](https://mlsanity.com/paper/2502.07557/) (2025)
- [HiddenDetect: Detecting Jailbreak Attacks against Large Vision-Language Models via Monitoring Hidden States](https://mlsanity.com/paper/2502.14744/) (2025)
- [Exploring Large Language Models for Feature Selection: A Data-centric Perspective](https://mlsanity.com/paper/2408.12025/) (2024)
- [Do Internal Layers of LLMs Reveal Patterns for Jailbreak Detection?](https://mlsanity.com/paper/2510.06594/) (2025)
- [Knowledge-Informed Automatic Feature Extraction via Collaborative Large Language Model Agents](https://mlsanity.com/paper/2511.15074/) (2025)
- [Jailbreak Detection in Clinical Training LLMs Using Feature-Based Predictive Models](https://mlsanity.com/paper/2505.00010/) (2025)
- [Machine Learning for Detection and Analysis of Novel LLM Jailbreaks](https://mlsanity.com/paper/2510.01644/) (2025)

## Abstract (arXiv)

Detecting jailbreak attempts in clinical training large language models (LLMs) requires accurate modeling of linguistic deviations that signal unsafe or off-task user behavior. Prior work on the 2-Sigma clinical simulation platform showed that manually annotated linguistic features could support jailbreak detection. However, reliance on manual annotation limited both scalability and expressiveness. In this study, we extend this framework by using experts' annotations of four core linguistic features (Professionalism, Medical Relevance, Ethical Behavior, and Contextual Distraction) and training multiple general-domain and medical-domain BERT-based LLM models to predict these features directly from text. The most reliable feature regressor for each dimension was selected and used as the feature extractor in a second layer of classifiers. We evaluate a suite of predictive models, including tree-based, linear, probabilistic, and ensemble methods, to determine jailbreak likelihood from the extracted features. Across cross-validation and held-out evaluations, the system achieves strong overall performance, indicating that LLM-derived linguistic features provide an effective basis for automated jailbreak detection. Error analysis further highlights key limitations in current annotations and feature representations, pointing toward future improvements such as richer annotation schemes, finer-grained feature extraction, and methods that capture the evolving risk of jailbreak behavior over the course of a dialogue. This work demonstrates a scalable and interpretable approach for detecting jailbreak behavior in safety-critical clinical dialogue systems.