Analysis of LLMs Against Prompt Injection and Jailbreak Attacks

Prompt attacks, including jailbreaks and prompt injections, pose a critical security risk to Large Language Model (LLM) systems. In production, guardrails must mitigate these attacks under strict low-latency constraints, resulting in a deployment gap in which lightweight classifiers and rule-based systems struggle to generalize under distribution shift, while high-capacity LLM-based judges remain too slow or costly for live enforcement. In this work, we examine whether lightweight, general-purpose LLMs can reliably serve as security judges under real-world production constraints. Through careful prompt and output design, lightweight LLMs are guided through a structured reasoning process involving explicit intent decomposition, safety-signal verification, harm assessment, and self-reflection. We evaluate our method on a curated dataset combining benign queries from real-world chatbots with adversarial prompts generated via automated red teaming (ART), covering diverse and evolving patterns. Our results show that general-purpose LLMs, such as gemini-2.0-flash-lite-001, can serve as effective low-latency judges for live guardrails. This configuration is currently deployed in production as a centralized guardrail service for public service chatbots in Singapore. We additionally evaluate a Mixture-of-Models (MoM) setting to assess whether aggregating multiple LLM judges improves prompt-attack detection performance relative to single-model judges, with only modest gains observed.

As Large Language Models evolve for user convenience, vulnerability to jailbreak attacks continues to be reported despite ongoing efforts in safety training. Traditional jailbreak techniques typically focus on a single prompt injection, neglecting the models' ability to remember the flow of conversation and the user's instructions. In this paper, we propose Persona Attack, a memory injection based jailbreak method that manipulates the model's context window through a step by step approach. Experimental results from applying Persona Attack to several widely used LLMs reveal that, as injections accumulate in memory, models increasingly prioritize these instructions over their internal safety alignment mechanisms. Furthermore, our experiments empirically demonstrate that the attack success rate varies not only according to the memory implementation of the model, but also combinations of instructions and can reach 95% under specific instruction configurations.

Large Language Models (LLMs) have achieved remarkable success but remain highly susceptible to jailbreak attacks, in which adversarial prompts coerce models into generating harmful, unethical, or policy-violating outputs. Such attacks pose real-world risks, eroding safety, trust, and regulatory compliance in high-stakes applications. Although a variety of attack and defense methods have been proposed, existing evaluation practices are inadequate, often relying on narrow metrics like attack success rate that fail to capture the multidimensional nature of LLM security. In this paper, we present a systematic taxonomy of jailbreak attacks and defenses and introduce Security Cube, a unified, multi-dimensional framework for comprehensive evaluation of these techniques. We provide detailed comparison tables of existing attacks and defenses, highlighting key insights and open challenges across the literature. Leveraging Security Cube, we conduct benchmark studies on 13 representative attacks and 5 defenses, establishing a clear view of the current landscape encompassing jailbreak attacks, defenses, automated judges, and LLM vulnerabilities. Based on these evaluations, we distill critical findings, identify unresolved problems, and outline promising research directions for enhancing LLM robustness against jailbreak attacks. Our analysis aims to pave the way towards more robust, interpretable, and trustworthy LLM systems. Our code is available at Code.