Multi-Turn Jailbreak Attacks

Multi-turn jailbreak attacks demonstrate that harmful intent can be distributed across dialogue, yet existing methods obscure what conversational mechanisms drive vulnerability. We introduce BLUEPRINT, a safety-evaluation framework separating a factorized social-influence strategy space from WORLDVIEWSIM, a cross-turn situational context module. Monte Carlo Tree Search optimizes turn-level combinations of 18 theory-grounded influence factors across a four-turn trajectory. Across six frontier models, BLUEPRINT achieves near-ceiling ASR on major open-weight and proprietary models, while requiring the fewest average queries (2.46). The resulting trajectories further reveal model-specific vulnerability among resistant targets: each responds to distinct influence factors and strategy transitions, yet all share a common recovery pathway-shifting toward concrete, executable task framing consistently escapes hard-refusal states. Ablations confirm operational cues matter most: making requests actionable has the largest impact, gain framing is unusually potent, and some legitimacy appeals can backfire. These findings suggest robust multi-turn safety requires monitoring not only harmful content, but also how dialogue state makes unsafe requests appear concrete and locally executable.

Frontier language models that refuse harmful single-turn prompts often comply when the same intent is reached gradually over many turns, making multi-turn attacks one of the least understood failure modes of large language models. Most automated red-teaming methods treat this as a generation problem: produce attacks that break the model. We argue it is better framed as a search problem: discover, organize, and iteratively refine a diverse archive of attack strategies, producing a structured map of how a target model fails rather than a list of one-off successes. We introduce EvoFlint, which applies evolutionary quality-diversity search to multi-turn red-teaming. Attack strategies are phased conversation plans, not raw prompts, and are evolved through LLM-driven mutation and crossover. A Pareto fitness over attack success rate and peak severity preserves selection signal from near-miss attacks. A risk-indexed archive runs novelty search with local competition over strategy description embeddings inside each cell, maintaining diversity without committing to a predefined style taxonomy. A generation-level memory accumulates target-model insights across the population and feeds them back into strategy generation. On the HarmBench-test split, EvoFlint reaches attack success rates of 35.8% on Claude Sonnet 4.6, 59.7% on GPT-5.4, and 94.3% on Qwen3-32B, alongside 98.7% on the older GPT-4o included as a baseline reference. The resulting archive, organized by risk category, exposes for each target which categories of harm its safety training has and has not covered.

Modern large language models (LLMs) operate in interactive multi-turn settings, making multi-turn jailbreaking a realistic threat model and an important setting for automated red teaming. A core challenge in learning multi-turn jailbreak attackers is credit assignment: different turns contribute differently to the final outcome, yet existing learning signals are often too coarse to identify their individual contributions. We propose decomposed credit GRPO (DC-GRPO), a unified turn-level credit assignment framework for Group Relative Policy Optimization in multi-turn jailbreak learning. DC-GRPO assigns a separate group-relative learning signal to each turn by combining immediate and future credit, avoiding the credit misassignment induced by broadcasting a single trajectory-level score across the dialogue. We instantiate this framework with static and dynamic weighting rules that differ in how the two credit sources are balanced while sharing the same turn-level structure. Across multiple victim LLMs and benchmarks, the dynamic- and static-weighted variants achieve average ASR5@3 scores of 98.26% and 97.88%, respectively, substantially outperforming the state-of-the-art methods, including SEMA (86.58%) and TROJail (86.23%). Their consistently strong performance indicates that the central empirical benefit comes from turn-level group-relative credit assignment rather than a particular weighting rule. Warning: This paper contains examples of harmful content.

Autonomous CLI agents can now execute hundreds of actions across multi-hour sessions: writing code, executing shell commands, browsing the web, and managing cloud infrastructure, all with minimal human oversight. Does greater autonomy invite greater risk? We introduce ANCHOR, an automated auditing framework that stress-tests CLI agents on illegal tasks grounded in public US court cases. ANCHOR deploys an auditor agent fine-tuned on dark personality data using supervised and reinforcement fine tuning. This auditor roleplays persistent malicious users who decompose tasks, reframe requests upon refusal, and adapt strategies across multi-turn interactions. Evaluating frontier CLI agents, we find that while they often refuse illegal tasks when prompted directly, compliance reaches 100% under persistent malicious interaction. When agents comply, they frequently exceed user requests, autonomously building infrastructure for large-scale harm, including catastrophic risk scenarios such as large-scale financial fraud and bioweapon development. These findings demonstrate that current alignment techniques are insufficient for autonomous agents and underscore the need for safety evaluations against persistent, adaptive malicious users. We release ANCHOR at https://github.com/garified/anchor

Multi-turn jailbreaks can evade turn-level moderation by spreading unsafe intent across a dialogue through gradual escalation, reframing, and role manipulation. We address multi-turn jailbreak detection as a conversation-level classification problem and introduce an efficient hierarchical detector that avoids expensive long-context concatenation while retaining cross-turn reasoning. The model encodes individual turns to form compact turn representations and applies a lightweight conversation module that captures dialogue dynamics and selectively attends to fine-grained evidence when needed. On a challenging evaluation benchmark of 14,038 conversations, our approach achieves an F1 of 0.9394, outperforming Claude Opus 4.7, the strongest competing baseline, by 0.07 while halving its false-positive rate. Ablation studies confirm that each architectural component contributes meaningfully, with combining cross-attention and self-attention in the conversation module yielding a 2.26 percentage point reduction in false-positive rate over the self-attention-only variant.

Tool-using LLM agents interact with the world through actions that persist state in artifacts (e.g., workspace files or logs). Consequently, jailbreak defenses must reason about cross-step composition rather than isolated text. Yet most existing attacks and defenses, including ``multi-turn'' jailbreaks such as Crescendo and Tree of Attacks,still assume a single contiguous conversation visible to the defender. This assumption breaks down in real agent pipelines, where enforcement is fragmented across tools, modules, and time, and where artifact provenance is often not tracked. We operationalize a deployment failure mode for tool-using LLM agents, the \emph{provenance gap}, and study reproducible triggers for it: \emph{Context-Fractured Decomposition} (CFD), a family of cross-context multi-step jailbreaks that preserve benign-looking intermediate artifacts from an early interaction and elicit harmful behavior much later, potentially in a different agent instance or workflow stage, via individually innocuous tool actions whose risk emerges only under delayed artifact-mediated composition. We instrument the failure mode with trace-level diagnostics and outline a verifiable mitigation direction (provenance lineage tagging). Across agent-system jailbreak benchmarks, CFD improves success rates by up to 28.3 percentage points over state-of-the-art baselines, even against strong single-turn judges. Disclaimer: This paper contains examples of harmful or offensive language.

Multi-turn jailbreak attacks pose a growing threat to LLMs by exploiting conversational dynamics such as gradual escalation and cross-turn coordination. Existing defenses either rely on costly retraining -- often degrading model utility -- or apply single-turn analysis independently at each turn, failing to capture how risk accumulates along interaction trajectories. We observe that safety behavior in multi-turn interaction is trajectory-dependent: dialogue history continuously reshapes the model's conditioning context, making it insufficient to evaluate each turn in isolation. Motivated by this insight, we present THRD, the first training-free framework that explicitly models temporal risk accumulation for multi-turn jailbreak defense. THRD integrates four modules: a Turn-level Risk Assessor (TRA) for instantaneous risk estimation, a Historical Context Analyzer (HCA) for cross-turn intent escalation detection, a Response Evaluator (RE) for identifying facilitative outputs, and a Decision Module that combines these signals through a time-evolving scoring mechanism with attenuation-based modulation and trend-aware adjustment. Experiments against state-of-the-art multi-turn attacks -- including tree-search-based and multi-agent collaborative methods -- across two target models show that THRD reduces ASR to 0.2--4.0% while preserving model utility within 1.5% degradation on MMLU and GSM8K. Ablation studies confirm non-redundant module contributions and stable cross-architecture generalization. Analysis of first rejection triggers reveals that over 70% of multi-turn attacks require Turn~2 or later to detect, validating the necessity of explicit temporal aggregation.

Multi-turn jailbreak attacks pose a growing threat to large language model (LLM) safety because they exploit feedback from auxiliary judge models to iteratively refine prompts toward harmful goals. Existing defenses largely detect or block unsafe content at individual turns or at the final response, leaving the judge-driven refinement loop intact and allowing attackers to extract informative feedback from intermediate interactions. We introduce D-Judge, a semantics-preserving output rewriting defense that intervenes directly in this loop by rewriting the victim LLM's responses before they are evaluated by the attacker's judge. By misaligning the judge's feedback signal without changing the meaning of the original response, D-Judge derails the attacker's prompt-refinement process, causing subsequent queries to be optimized against a distorted signal of attack progress. To improve D-Judge's ability to produce such rewrites, we construct a dataset of semantically equivalent response pairs that induce different judge-assigned harmfulness scores, and use it for supervised fine-tuning followed by direct preference optimization. Experiments on HarmBench show that D-Judge reduces the success rate of state-of-the-art multi-turn jailbreaks while preserving performance on benign benchmarks.

Patient-facing medical chatbots are commonly evaluated on single-turn prompts, yet real users push back after refusals, add urgency, and invoke authority. We introduce MultiTurnPSB, a four-turn adversarial extension of PatientSafetyBench, and evaluate GPT-4.1-mini under fixed template, template-adaptive, and live adversarial attacks. Unsafe responses rise from 35% to nearly 80% by Turn 4 under live attack. Under the same adversary, GPT-4.1-mini and Claude Sonnet 4.5 are statistically indistinguishable at baseline but diverge to a 19x gap by Turn 4, a difference invisible to single-turn evaluation. We characterize four degradation trajectory signatures and identify a two-element attack formula responsible for most catastrophic failures. A lightweight input-side classifier reduces Turn 4 unsafe responses by 52 percentage points despite severe accuracy degradation, but the 45% false alarm rate on benign queries is the primary deployment constraint. A methodological finding also emerges: Claude Sonnet refused to generate adversarial messages in over half of late-turn conversations despite explicit red team framing, suggesting safety training may generalize to the attacker role.

Safety defenses for large language models (LLMs) are typically trained and evaluated on single-turn prompts, yet real attacks often unfold as indirect, multi-turn probing. To defend against this more nuanced form of deception, we present a unified pipeline that generates realistic multi-turn deceptive question sets via multi-objective genetic prompt optimization with co-evolving mutation operators. We validate this dataset through a human study, which also revealed that early generations yielded the most convincing deception and practical constraints such as adherence filtering and ordering effects. Using this data, we were able to detect deceptive attempts to access prohibited information using simple, explainable geometric signals in embedding space coupled with a lightweight feed-forward classifier. Three geometric features (angular coverage, distance ratio, and linearity) augmented with pairwise similarity statistics led to a compact predictive model that achieved consistently high recall (0.89) across base, reworded, and truncated (three-turn) scenarios, with test-time F1 ranging from 0.74-0.86. The results support a central hypothesis that multi-turn deceptive intent leaves a stable geometric footprint that enables lightweight, transparent screening without expensive end-to-end training. We further discuss responsible uses, limitations, and paths toward larger, more diverse human-evaluated datasets. The primary contribution to artificial intelligence is the multi-objective evolutionary framework for prompt generation, and the engineering application is the deployment of a lightweight geometric detection system for LLM safety infrastructure.

In this work, we propose BAIT (Boundary-Aware Iterative Trap), a three-step jailbreak framework that elicits malicious information through internal disclosure by target large language models (LLMs), instead of external feedback from judge LLMs. BAIT first asks the model to identify the protection boundary, then requires it to refine that boundary, and finally requests a detailed example. By expanding each step upon the model's previous responses, BAIT turns the model's own reasoning and consistency tendency into a disclosure pathway. Experiments on AdvBench, JailbreakBench, AIR-Bench, and SORRY-Bench demonstrate that BAIT consistently achieves strong attack success rates across top-tier large language models, significantly advancing conventional jailbreak baselines. Further analysis reveals that: 1) prevention-oriented framing significantly outperforms direct knowledge requests; 2) the refinement step plays a critical role in disclosure escalation; and 3) the first two steps have a certain chance of eliciting harmful content while triggering little filtering. These findings underscore the necessity of safeguarding against internally driven reasoning trajectories that progressively cross safety boundaries.

Multi-turn jailbreaks exploit the ability of large language models to accumulate and act on conversational context. Instead of stating a harmful request directly, an attacker can gradually steer the conversation toward an unsafe answer. Recent methods demonstrate this risk, but they are usually evaluated as black-box pipelines with different budgets, judges, retry rules, and strategy generation procedures. As a result, it is often unclear whether reported gains reflect stronger attack mechanisms or different experimental conditions. We introduce MT-JailBench, a modular evaluation framework for benchmarking multi-turn jailbreaks under fixed conditions. MT-JailBench implements each attack as five interacting modules: evaluation function, attack strategy, prompt generation, prompt refinement, and flow control. This design enables fair comparison across attack methods and component-wise analysis of what drives attack success. Using MT-JailBench, we find that resource budgets and evaluation functions are major confounders: controlling turns, retries, interactions, sampled strategies, and judges substantially change the ranking of attacks. At the component level, prompt generation accounts for most performance variation, while refinement and flow control provide moderate gains. We also find that explicit dynamic strategy generation is not always necessary; stochastic sampling from a fixed strategy can rival more elaborate diversification mechanisms. Finally, recomposing the best components yields a strong attack configuration that outperforms its source attacks and generalizes across diverse target LLMs. MT-JailBench therefore provides a modular framework for comparing multi-turn jailbreaks, understanding the impact of components, and guiding stronger red-teaming evaluations.

Deploying LLMs in multi-turn dialogues facilitates jailbreak attacks that distribute harmful intent across seemingly benign turns. Recent training-based multi-turn jailbreak methods learn long-horizon attack strategies from interaction feedback, but often rely on coarse trajectory-level outcome signals that broadcast uniformly to every turn. However, we find that turn-level contributions in multi-turn jailbreaking are non-uniform, phase-dependent, and target-specific. Such coarse outcome supervision induces a credit assignment problem, leading to over-rewarding redundant turns in successful trajectories and under-crediting useful intermediate turns in failed ones. To address this, we propose TRACE, a turn-aware credit assignment framework for reinforcement learning (RL)-based multi-turn jailbreaking. For successful trajectories, TRACE estimates turn-level contributions via leave-one-turn-out semantic masking; for failed ones, TRACE assigns penalties based on prompt harmfulness and semantic relevance, with an additional local refusal-aware penalty. Furthermore, we reuse the attack-side credit signal for multi-turn defense alignment. Extensive experiments on open-source and closed-source targets show that TRACE achieves strong overall performance in effectiveness, transferability, and efficiency, yielding about a 25% relative improvement in attack success rate over the strongest RL baseline while also improving the safety-utility balance when reused for defense alignment.

Many-shot jailbreaking (MSJ) causes safety-aligned language models to answer harmful queries by preceding them with many harmful question-answer demonstrations. We study why this attack becomes stronger as the number of demonstrations increases. Empirically, we find that MSJ induces a progressive activation drift: the representation of a fixed harmful query moves step by step away from the safety-aligned region as more harmful demonstrations are added. Theoretically, we show that this drift can be interpreted as implicit malicious fine-tuning: conditioning on N harmful demonstrations induces SGD-style updates equivalent to optimizing on the corresponding N harmful samples. This view turns the attack mechanism into a defense principle. We append a fixed one-shot safety demonstration at inference time, which induces a counteracting safety-oriented update and restores refusal behavior. The resulting method improves the model's robustness to MSJ without modifying its parameters or requiring white-box access at deployment. Code is available at https://github.com/Thecommonirin/SafeEnd.

Hidden malicious intent in multi-turn dialogue poses a growing threat to deployed large language models (LLMs). Rather than exposing a harmful objective in a single prompt, attackers can distribute their intent across multiple benign-looking turns, making defense a problem not only of whether a dialogue is harmful, but also of when intervention becomes necessary. Existing trace-level labeling approaches provide only coarse safety signals and do not identify this intervention boundary, making it difficult to distinguish timely intervention from premature refusal or a block that comes too late. This work introduces turn-level harm-enabling supervision for multi-turn defense. We define the earliest harm-enabling turn as the first point at which delivering a candidate response would make the accumulated interaction sufficient to enable harmful action. To instantiate this supervision at scale, we construct the Multi-Turn Intent Dataset (MTID), which contains adaptive attack rollouts, matched benign hard negatives, and annotations of this boundary. Using MTID, we train TurnGate, a response-aware monitor that learns when to intervene, and further optimize its policy through multi-turn reinforcement learning. Experiments show that turn-level boundary supervision improves intervention localization, while reinforcement learning further improves the safety--utility trade-off. TurnGate outperforms existing guardrails and multi-turn monitoring baselines, and generalizes across risk domains, attacker pipelines, and target models. Our code is available at https://github.com/Graph-COM/TurnGate.

Large language models (LLMs) remain vulnerable to jailbreak attacks that bypass safety alignment and elicit harmful responses. A growing body of work shows that contextual priming, where earlier turns covertly bias later replies, constitutes a powerful attack surface, with hand-crafted multi-turn scaffolds consistently outperforming single-turn manipulations on capable models. However, automated optimization-based red-teaming has remained largely limited to the single-turn setting, iterating over static prompts and lacking the ability to reason about which forms of conversational priming induce compliance. While recent multi-turn, search-based approaches have begun to bridge this gap, the mutator design space underlying effective primed dialogues remains largely unexplored. We present ContextualJailbreak, a black-box red-teaming strategy that performs evolutionary search over a simulated multi-turn primed dialogue. The strategy leverages a graded 0-5 harm score from a two-level judge as an in-loop signal, enabling partially harmful responses to guide the search process rather than being discarded. Search is driven by five semantically defined mutation operators: roleplay, scenario, expand, troubleshooting, and mechanistic, of which the last two are novel contributions of this work. Across 50 representative HarmBench behaviors, ContextualJailbreak achieves an ASR of 100% on gpt-oss:20B, 100% on qwen3-8B, 100% on llama3.1:70B, and 90% on gpt-oss:120B, outperforming four single- and multi-turn baselines by 31-96 percentage points on average. The 40 maximally harmful attacks discovered against gpt-oss:120B transfer without adaptation to closed frontier models, achieving 90.0% on gpt-4o-mini, 70.0% on gpt-5, and 70.0% on gemini-3-flash, but only 17.5% on claude-opus-4-7 and 15.0% on claude-sonnet-4-6, revealing a pronounced provider-level asymmetry in alignment robustness.

We present MultiBreak, a scalable and diverse multi-turn jailbreak benchmark to evaluate large language model (LLM) safety. Multi-turn jailbreaks mimic natural conversational settings, making them easier to bypass safety-aligned LLM than single-turn jailbreaks. Existing multi-turn benchmarks are limited in size or rely heavily on templates, which restrict their diversity. To address this gap, we unify a wide range of harmful jailbreak intents, and introduce an active learning pipeline for expanding high-quality multi-turn adversarial prompts, where a generator is iteratively fine-tuned to produce stronger attack candidates, guided by uncertainty-based refinement. Our MultiBreak includes 10,389 multi-turn adversarial prompts, spans 2,665 distinct harmful intents, and covers the most diverse set of topics to date. Empirical evaluation shows that our benchmark achieves up to a 54.0 and 34.6 higher attack success rate (ASR)} than the second-best dataset on DeepSeek-R1-7B and GPT-4.1-mini, respectively. More importantly, safety evaluations suggest that diverse attack categories uncover fine-grained LLM vulnerabilities}, and categories that appear benign under single-turn can exhibit substantially higher adversarial effectiveness in multi-turn scenarios. These findings highlight persistent vulnerabilities of LLMs under realistic adversarial settings and establish MultiBreak as a scalable resource for advancing LLM safety.

Large (vision-)language models exhibit remarkable capability but remain highly susceptible to jailbreaking. Existing safety training approaches aim to have the model learn a refusal boundary between safe and unsafe, based on the user's intent. It has been found that this binary training regime often leads to brittleness, since the user intent cannot reliably be evaluated, especially if the attacker obfuscates their intent, and also makes the system seem unhelpful. In response, frontier models, such as GPT-5, have shifted from refusal-based safeguards to safe completion, that aims to maximize helpfulness while obeying safety constraints. However, safe completion could be exploited when a user pretends their intention is benign. Specifically, this intent inversion would be effective in multi-turn conversation, where the attacker has multiple opportunities to reinforce their deceptively benign intent. In this work, we introduce a novel multi-turn jailbreaking method that exploits this vulnerability. Our approach gradually builds conversational trust by simulating benign-seeming intentions and by exploiting the consistency property of the model, ultimately guiding the target model toward harmful, detailed outputs. Most crucially, our approach also uncovered an additional class of model vulnerability that we call para-jailbreaking that has been unnoticed up to now. Para-jailbreaking describes the situation where the model may not reveal harmful direct reply to the attack query, however the information that it reveals is nevertheless harmful. Our contributions are threefold. First, it achieves high success rates against frontier models including GPT-5-thinking and Claude-Sonnet-4.5. Second, our approach revealed and addressed para-jailbreaking harmful output. Third, experiments on multimodal VLM models showed that our approach outperformed state-of-the-art models.

Large language models (LLMs) are increasingly integrated into sensitive workflows, raising the stakes for adversarial robustness and safety. This paper introduces Transient Turn Injection(TTI), a new multi-turn attack technique that systematically exploits stateless moderation by distributing adversarial intent across isolated interactions. TTI leverages automated attacker agents powered by large language models to iteratively test and evade policy enforcement in both commercial and open-source LLMs, marking a departure from conventional jailbreak approaches that typically depend on maintaining persistent conversational context. Our extensive evaluation across state-of-the-art models-including those from OpenAI, Anthropic, Google Gemini, Meta, and prominent open-source alternatives-uncovers significant variations in resilience to TTI attacks, with only select architectures exhibiting substantial inherent robustness. Our automated blackbox evaluation framework also uncovers previously unknown model specific vulnerabilities and attack surface patterns, especially within medical and high stakes domains. We further compare TTI against established adversarial prompting methods and detail practical mitigation strategies, such as session level context aggregation and deep alignment approaches. Our study underscores the urgent need for holistic, context aware defenses and continuous adversarial testing to future proof LLM deployments against evolving multi-turn threats.

Multi-turn jailbreak attacks progressively erode LLM safety alignment across seemingly innocuous conversation turns, achieving success rates exceeding 90% against state-of-the-art models. Existing alignment-based and guardrail methods suffer from three key limitations: they require costly weight modification, evaluate each turn independently without modeling cumulative safety erosion, and detect attacks only after harmful content has been generated. To address these limitations, we first formulate the proactive early jailbreak detection problem with a new metric, detection lead, that measures how early an attack can be detected before the LLM complies. We then propose SAFEDREAM, a lightweight world-model-based framework that operates as an external module without modifying the LLM's weights. SAFEDREAM introduces three components: (1) a safety state world model that encodes LLM hidden states into a compact safety representation and predicts how it evolves across turns, (2) CUSUM detection that accumulates weak per-turn risk signals into reliable evidence, and (3) contrastive imagination that simultaneously rolls out attack and benign futures in latent space to issue early alarms before jailbreaks occur. On three multi-turn jailbreak benchmarks (XGuard-Train, SafeDialBench, SafeMTData) against 8 baselines, SAFEDREAM achieves the best detection timeliness across all benchmarks (1.06-1.20 turns before compliance) while maintaining competitive false positive rates and outperforming baselines in detection quality.

Safety evaluation of multimodal large language models requires tracking not only whether an attack succeeds, but also how the interaction unfolds across turns and input modalities. We present MUSE (Multimodal Unified Safety Evaluation), an open-source, browser-based, run-centric platform for multimodal safety evaluation. MUSE treats each attack run as the persistent unit of execution, inspection, and analysis, preserving its configuration, multi-turn trajectory, delivered modalities and media, target responses, and safety judgments. A five-level response taxonomy further distinguishes full Compliance from Partial Compliance and refusal behavior, yielding hard ASR, soft ASR, and gray-zone width (GZW). Across 11,700 evaluations on six multimodal LLMs, direct text-only requests yield only 3.1% macro hard ASR and 4.4% soft ASR, while iterative attack procedures are substantially more effective. Attack effectiveness also varies substantially with the attacker backbone. In contrast, Inter-Turn Modality Switching (ITMS), evaluated as a controlled delivery-modality probe, does not consistently increase attack success. These results demonstrate the value of run-centric, fine-grained evaluation for characterizing multimodal safety behavior beyond a single binary success metric.

Large Language Model (LLM) agents are powering a growing share of interactive web applications, yet remain vulnerable to misuse and harm. Prior jailbreak research has largely focused on single-turn prompts, whereas real harassment often unfolds over multi-turn interactions. In this work, we present the Online Harassment Agentic Benchmark consisting of: (i) a synthetic multi-turn harassment conversation dataset, (ii) a multi-agent (e.g., harasser, victim) simulation informed by repeated game theory, (iii) three jailbreak methods attacking agents across memory, planning, and fine-tuning, and (iv) a mixed-methods evaluation framework. We utilize two prominent LLMs, LLaMA-3.1-8B-Instruct (open-source) and Gemini-2.0-flash (closed-source). Our results show that jailbreak tuning makes harassment nearly guaranteed with an attack success rate of 95.78--96.89% vs. 57.25--64.19% without tuning in Llama, and 99.33% vs. 98.46% without tuning in Gemini, while sharply reducing refusal rate to 1-2% in both models. The most prevalent toxic behaviors are Insult with 84.9--87.8% vs. 44.2--50.8% without tuning, and Flaming with 81.2--85.1% vs. 31.5--38.8% without tuning, indicating weaker guardrails compared to sensitive categories such as sexual or racial harassment. Qualitative evaluation further reveals that attacked agents reproduce human-like aggression profiles, such as Machiavellian/psychopathic patterns under planning, and narcissistic tendencies with memory. Counterintuitively, closed-source and open-source models exhibit distinct escalation trajectories across turns, with closed-source models showing significant vulnerability. Overall, our findings show that multi-turn and theory-grounded attacks not only succeed at high rates but also mimic human-like harassment dynamics, motivating the development of robust safety guardrails to ultimately keep online platforms safe and responsible.