Penetration Testing

AI-driven penetration testing has been demonstrated with premium frontier models such as GPT-4, but the per-engagement token cost makes continuous, automated testing unaffordable for the smaller organisations that need it most. This paper presents PentestChain, a ten-phase automated penetration testing framework that couples a curated, deterministic exploit map with a cost-aware AI cascade-a local Ollama model (qwen2.5-7b) first, then free-tier OpenRouter and Cerebras, with a rule-based fallback that always produces output-and exposes the full pipeline through a Model Context Protocol (MCP) server with eleven tools. We make three contributions. First, we treat US-dollar cost per engagement as a measured, first-class evaluation metric and show that a 7B-parameter local model, kept off the critical path by a deterministic backbone, sustains end-to-end operation at zero measured paid-API cost. Second, we analyse the attack surface that an MCP-exposed offensive engine introduces, grounding a four-position threat model in the 2025 MCP incident record (the CVE-2025-6514 remote-code-execution flaw in mcp-remote, the postmark-mcp supply-chain backdoor, and the tool-poisoning-rug-pull-line-jumping class), and contribute four mitigations. Third, we specify a reproducible, containerised evalua-tion protocol aligned with the standardised testbeds now expected at top-tier venues-AutoPenBench, a Cybench subset, and the PentestGPT 182-sub-task benchmark-with multi-trial statistics (more than 10 trials per configuration, pass-at-k, non-parametric significance tests and effect sizes) and direct, same testbed reproduction of the PentestGPT and PentestAgent baselines rather than citation of their published numbers. On the legacy targets measured to date, the framework detected 26 services, enriched 34 CVEs, produced

Logic attack graphs grounded in scanner output provide explicit and auditable attack path reasoning LLM-based agents lack. Integrating symbolic frameworks such as MulVAL to contemporary security workflows or agentic pipelines, however, requires translating scanner evidence to initial facts, and creating domain-specific rules. We present a semi-automated pipeline that addresses this interoperability problem and depict its feasibility in a web-security case study. Our pipeline parses findings from Trivy, Semgrep, and Nmap into MulVAL predicates and uses an LLM-assisted process to construct domain-specific Datalog rules linking scanner-detectable evidence to attack techniques. MulVAL/XSB then performs symbolic inference to generate structured attack paths. We evaluate the attack-graph construction infrastructure on 54 web Capture-the-Flag tasks from CyBench within an agentic pipeline (Hybrid Reasoner); we do not evaluate the performance of the downstream agent. Every task produced at least one goal-reaching graph, and we achieve mean ground-truth vulnerability coverage of 53.7%, with 51.9% achieving full coverage; mean noise-path rate was 83.9%. With median end-to-end time of 24.9 s (MulVAL reasoning: 2.7 s) the pipeline is feasible and runtime-practical for agentic workflows, but predicate coverage, rule coverage, and path precision remain limiting factors. Next steps include semantic rule validation and agent-level comparison for graph-guided pentesting.

Large language model (LLM) based agents are increasingly applied to cybersecurity tasks such as vulnerability discovery and automated penetration testing. On long-horizon security tasks, however, such agents remain limited by context forgetting and intent drift: early critical facts and causal reasoning chains are lost over extended interactions, and the agent falls into aimless, repetitive exploration. This paper proposes Intentest, an intent-graph-guided automated penetration testing agent that externalizes long-horizon state from the LLM's context window onto a persistent fact-intent directed acyclic graph (DAG), thereby substantially reducing invalid transitions. We evaluate Intentest on automated penetration testing of web applications, a representative long-tail task in cybersecurity. In the DAG, verified network states are stored as immutable fact nodes, and exploration directions are constrained as intent edges bounded by predecessor facts. The system adopts a three-layer architecture, in which the fact-intent mapping layer maintains the global state, the task scheduling and allocation layer ensures execution stability through two-phase degradation recovery and multi-dimensional adaptive load balancing, and the intent retrieval and prediction layer provides tactical priors through a top-down five-stage filtering algorithm. On a benchmark of real CTF challenges covering more than ten vulnerability types across three difficulty levels, Intentest achieves an overall success rate of 88.2% and a success rate of 75.0% on hard tasks, improving over the baseline by approximately 44 and 50 percentage points. Ablation experiments further show that the intent retrieval and prediction reduce the average number of rounds on successful medium and hard tasks by about 33% and 48%, respectively, without changing the set of solvable tasks.

Large language model (LLM) agents automate penetration testing through an observation-action loop, selecting actions based on observations returned by tools. This dependence allows defenders to inject deceptive observations that can mislead the agent's decision-making process. However, existing defenses rely heavily on static, isolated artifacts planted in the environment prior to an attack. Advanced agents can progressively recognize and bypass these artifacts, ultimately refocusing their exploitation attempts on the real target. To address this issue, we introduce AgentSnare, a trajectory-adaptive deception system that dynamically unfolds a decoy environment to continually steer the penetration agent away from the real target. Specifically, AgentSnare employs an artifact-construction policy model that constructs candidate artifacts conditioned on the agent's interaction history and decoy state. AgentSnare then validates these candidates and incrementally incorporates valid artifacts into a factually consistent decoy environment, thereby delaying the attack by absorbing its tool calls, diverting its post-entry trajectory within the decoy, and defusing it by inducing completion reports grounded in decoy evidence. Across 15 CVE-Bench web applications and three attacker models, AgentSnare absorbs 46.8% of the agent's tool calls in the decoy and retains 55.9% of post-entry actions there, while 90.0% of completion attempts are grounded in decoy evidence; across all 45 attacker-CVE pairs, no real target is successfully exploited at pass@3.

Traditional pentesting uses reconnaissance at each step to uncover unseen weaknesses, build stronger attacks, and advance the objective; we argue that AI agents require the same treatment. We formalize agent reconnaissance by modeling the process and identifying the knowledge assets it seeks to extract: what they are, how they are used, and which agent weaknesses they exploit to give adversaries leverage in indirect prompt injection attacks. We instantiate these insights in Know Your Agent (KYA), a framework that automates black-box, reconnaissance-driven pentesting by probing agents, building target profiles, and using those profiles to craft stronger attacks. We evaluate KYA on agent-security benchmarks and a real-world coding agent, and release KYA, its benchmarks, and baseline implementations for reproducibility.

Penetration testing traditionally evaluates whether adversaries can exploit weaknesses in software, infrastructure, configurations, or operational controls to achieve security-relevant compromise. This paradigm remains necessary for AI-enabled systems, but it is no longer sufficient. In such systems, adversaries may influence prompts, retrieved content, sensor inputs, training data, memory, tools, or human-AI interaction loops to alter system behavior without directly compromising the underlying infrastructure. This paper reframes penetration testing for AI-enabled systems as objective-driven behavioral evaluation. We define an AI-enabled system as one in which learned models materially influence behavior affecting operational outcomes, and we define AI-enabled penetration as the feasible induction of AI-governed behavior that violates one or more operational objectives under an explicit threat model. This definition preserves conventional penetration testing while extending it to adversarial pathways such as prompt injection, indirect prompt injection, data poisoning, sensor manipulation, retrieval poisoning, tool misuse, and agentic misalignment. We further propose a testing workflow that identifies operational objectives, maps AI-governed behavior, analyzes adversarial influence surfaces, defines behavioral failure criteria, executes scenario-based tests, and reports evidence linking adversarial action to objective violation. A running example involving an AI-enabled security operations center assistant illustrates how penetration may occur through behavioral influence rather than infrastructure compromise. Together, the definitions, workflow, and example provide a technical framework for evaluating adversarial success in deployed AI-enabled systems.

Recent autonomous penetration testing papers report high benchmark scores while adding multi-component security harnesses around frontier LLMs. Because these systems often change both architecture and backbone model, it is difficult to tell how much performance comes from the harness rather than from the underlying model. This paper presents a controlled study on the 104-task XBOW benchmark using default coding CLI agents as plain-agent baselines. We first run Codex, OpenCode, and Pi with the same GPT-5 model, budget, target interface, and scoring rule. This phase identifies the strongest same-model baseline and tests whether security-specific prompt variants improve its observed score. We then compare the default Codex scaffold with published MAPTA and PentestGPT V2 results under the closest available model matches. Finally, we repeat the plain-agent experiment with GPT-5.2 and GPT-5.5 to measure model scaling inside the same scaffold. The results show a mixed but practical picture. Specialised harnesses can add measurable benchmark lift and may improve cost efficiency, but plain coding agents already solve a large share of the benchmark; repeated plain-agent runs can match or exceed some published architecture scores in union coverage, and newer models substantially improve the same scaffold. Future evaluations should report model-matched plain-agent baselines before attributing benchmark gains to architecture design alone.

Internet of Things (IoT) systems are inherently vulnerable due to constrained hardware, outdated firmware, and insecure default configurations, creating a need for scalable and adaptive security testing approaches. While recent adoptions of Large Language Model (LLM) agents have demonstrated promise in penetration testing and Capture-the-Flag (CTF) environments, their application to IoT specific vulnerabilities remains unexplored. This paper presents an autonomous multi-agent framework, referred to as Vulnerability EXploitation using AI Agents (VEXAIoT), for vulnerability discovery and exploitation in IoT environments using LLM-based reasoning and offensive security tools. The framework combines a vulnerability detection agent and an attack execution agent to perform reconnaissance, plan attack sequences, and execute exploits against vulnerable IoT services. The system is evaluated in IoTGoat and Metasploitable environments across ten attack scenarios mapped to OWASP IoT vulnerabilities. Experimental results show attack success rate of up to 100% with low token overhead and average execution times under two minutes for most attacks. Across 260 attack executions, VEXAIoT achieves a 95.0% overall success rate, including 94.5% success in IoTGoat and 96.7% success in Metasploitable2. These results demonstrate the potential for LLM-driven agents to automate IoT vulnerability assessment and offensive security workflows in controlled environments

Supervised deep learning has been widely used for weld penetration state classification; however, its performance often degrades significantly under domain shift, such as when transferring models between welding processes with distinct physical mechanisms:for instance, from arc-dominated tungsten inert gas (TIG) welding to keyhole-based laser welding. To overcome this limitation, we propose an unsupervised domain adaptation (UDA) framework integrated with a gradual source domain expansion (GSDE) strategy. Evaluated on dedicated TIG and laser welding datasets, our approach achieves high accuracy in both same-process and cross-process transfer tasks. Specifically, it attains average accuracies of 90.65% on TIGFH and 90.72% on LSPS in same-process settings, surpassing a supervised baseline by 35.83% and 38.87%, respectively. More notably, in cross-process scenarios, it reaches 80.48% for TIG to Laser and 81.13% for Laser to TIG, improving upon the baseline by 43.39% and 43.40%. UMAP visualizations verify that the model learns domain-invariant features while maintaining discriminative class boundaries. This method considerably lowers the relabeling cost for new welding processes and enhances the versatility of intelligent monitoring across different welding systems.

The laser welding full-penetration is of critical importance, as it constitutes one of the fundamental factors in achieving defect-free welded joints. Accurate prediction of the penetration state is therefore essential for ensuring weld quality. To this end, this paper introduces SimPhysNet, a novel algorithm that achieves high classification accuracy in laser welding penetration prediction using only a limited number of labelled images. This approach effectively overcomes the limitations of supervised learning classification algorithms, which are hindered in industrial applications by their dependence on extensive, high-quality labelled data. The core of SimPhysNet is a unique self-supervised learning paradigm that embeds physical priors into a contrastive learning framework. By incorporating a physics-informed neural network (PINN), the model is guided to extract physically meaningful features of the molten pool and keyhole from a large set of unlabelled data, while three image augmentation tasks further enhance its generalization capabilities. Subsequently, a few-shot learning strategy, based on prototypical networks, enables robust classification by constructing class representations from a minimal set of labelled images. Experimental results demonstrate that SimPhysNet achieves a classification accuracy of 96.06% using only 200 labelled images (approximately 5% of the total labelled dataset), which is comparable to the performance of conventional supervised learning algorithms that utilize the entire labelled dataset. This work presents a new, efficient, and highly accurate method, providing the way for the intelligent automation of laser welding.

Large Language Models (LLMs) have shown promise for automated penetration testing, yet existing end-to-end black-box evaluations are highly susceptible to error cascading: failures in early reconnaissance can mask an agent's actual ability to exploit vulnerabilities. To more accurately characterize these capabilities, we propose a two-stage decoupled evaluation framework that separates exploit execution from reconnaissance. Using ground-truth injection and knowledge-driven ablation across 70 high-fidelity web vulnerability testbeds, our framework isolates exploitation performance from reconnaissance noise. We empirically evaluate five open-source penetration-testing agents, covering multiagent, monolithic, and graph-driven architectures, on a strictly aligned subset of 50 representative vulnerabilities. The results reveal a substantial capability gap. With accurate vulnerability context, agents achieve a functional success rate of up to 90.0%, whereas autonomous reconnaissance, measured by targeted vulnerability recall, plateaus at approximately 50.0%, primarily due to failures in parsing unstructured telemetry. Cross-architectural analysis further reveals distinct capability niches: multi-agent isolation is more effective for long-sequence interactions such as de-serialization, while monolithic and graph-driven designs perform better on short-chain injections and cross-session access-control vulnerabilities, respectively. This decoupled evaluation work provides a fine-grained benchmarking protocol and an empirical basis for designing next-generation automated offensive security agents.

Nowadays, the autonomous execution of cyberattacks capable of causing substantial real-world harm is widely regarded as one of the critical red lines that frontier AI systems must not cross. Within this broader red-line scenario, autonomous penetration represents a core enabling capability and subtask: the ability of LLM-powered AI systems to independently conduct adversarial operations against a target server without human intervention, identify and exploit vulnerabilities, and obtain unauthorized access or control. A growing body of work has sought to assess the autonomous penetration capabilities of AI systems. However, existing evaluations often employ opaque methodologies, rely on unrealistic or overly simplified penetration-testing scenarios, or provide LLMs with excessive prior knowledge and task-specific guidance, and cannot accurately capture the extent to which modern AI systems can autonomously perform this core capability within broader high-impact cyberattack scenarios. To address these limitations, we construct a new autonomous penetration evaluation framework consisting of two components: target servers and agent scaffolding. Specifically, on the target-server side, we design two levels of target environments based on the number of secure services without known vulnerabilities deployed alongside a vulnerable service: Tier1 (one secure service) and Tier2 (three secure services), resulting in a total of 300 target servers. Meanwhile, the agent scaffolding adopts a general-purpose agent architecture equipped with a set of general-purpose cybersecurity tools, without any target-specific prior knowledge. We evaluate 19 open-weight and proprietary LLMs, and find that current models achieve penetration success rates ranging from 10.7% to 69.3%. Moreover, we observe that autonomous penetration capability continues to improve alongside advances in overall model capability.

LLM-driven automated penetration testing agents are typically evaluated against static targets that neither detect nor respond to attacks, so their behavior under intelligent defense remains untested. The causal consistency of multi-step attack chains likewise hinges on unstable LLM reasoning, and agent decisions remain opaque to human analysts. These three shortcomings, in realism, consistency, and auditability, are usually patched in isolation. We present ZERO-APT, a turn-based attacker-defender-judge framework that addresses them within a single architecture. For realism, ZERO-APT embeds a configurable LLM Defender that consumes Sysmon telemetry and detects attacks in real time, exposing the attacker to a live opponent rather than a passive target. For consistency, three architectural mechanisms move causal consistency from unstable LLM reasoning into enforced system architecture: separation of planning from execution, multi-dimensional ReAct feedback, and a hard-constraint-filtered action library. For auditability, a dedicated Judge agent adjudicates each round, maintains global state, and emits structured post-hoc CTI reports that make every decision traceable. We evaluate a Windows Server 2022 post-exploitation prototype across five scenarios with three Defender configurations. ZERO-APT reaches 79% attack success rate (Aurora 22%, PentestGPT 39%), a Causal Consistency Score of 0.860 (Aurora 0.930, Claude Code 0.520), and end-to-end decision auditability through structured CTI reports. We release the benchmark to support evaluation of penetration agents under intelligent defense.

Large language models (LLMs) can autonomously conduct multi-stage cyber attacks, but the consistency of their offensive behavior under repeated trials remains unstudied. This work presents the first large-scale empirical measurement of LLM attack consistency: 400 autonomous penetration testing runs (4 models, 100 each) against an identical honeypot hosting OWASP Juice Shop and two additional vulnerable services, holding prompt, orchestrator, and target constant. No model emitted a content refusal that survived the orchestrator's one-shot authorization re-prompt at iterations 0-1. Claude Sonnet 4's API calls did encounter upstream service unavailability - 91 of 1,135 calls returned HTTP 529 overloaded_error during a documented Anthropic capacity event, truncating 39 of 100 Claude runs. An earlier draft catalogued these as safety refusals; on full-log audit they are upstream API failures, not model-level refusals. Despite this, Claude achieved full exploitation in 61 of 100 runs; Gemini 2.5 Flash-Lite in 85; GPT-4o-mini in 56 while deploying 98 unique attack strategies; qwen2.5-coder:14b in 25. Failure modes are model-distinctive: Claude through API truncation (39 runs), qwen through premature completion (52), GPT-4o-mini through iteration-budget exhaustion (23). Cross-service credential reuse appeared only in configurations retaining the most conversation history (qwen 57%, GPT-4o-mini 49%, cloud models 0% on 5-exchange windows). Cross-model exploitation rate differences are statistically significant (p < 0.001) with large effect sizes; qwen vs. Gemini SQL injection rates differ at Cohen's h = 1.12. First-exploit timing fell within a 15-30 second wall-clock range. To our knowledge, this is the first study to measure autonomous LLM attack behavior at N=100 per model across a multi-service target.

Honeypots are decoy systems mimicking real system components designed to defend against cyber attacks. Recently, LLMs increasingly serve as simulation backbones for honeypots. They enable defenders to construct high-interaction honeypots with low system security risks. However, LLM-powered honeypot development lacks a unified evaluation framework. Most evaluations consist of measuring response similarity on fixed commands, manual testing, or real-world deployment. These methods are often not scalable for development, reproducible across evaluations, representative of practical attacks, or adaptable to various attacker and honeypot configurations. In this work, we bridge this gap and propose Honeyval, a comprehensive evaluation framework for LLM-powered HTTP honeypots. We address the limitations of prior evaluations by grounding the honeypots in 16 backend applications, using AI hacking agents as attackers, employing two control tasks to monitor agent and honeypot capabilities across customizations, and defining clear and verifiable exploit goals for the attacker. Using Honeyval, we conduct an extensive evaluation of recent cost-efficient LLMs as HTTP honeypots. Our experiments highlight the promise of LLM-powered honeypots; they lead to substantially longer interactions with the attacker than rule-based baseline honeypots and are far less frequently detected even by frontier models, all while, on average, preserving a running cost advantage against agentic attackers. Further, we experiment with different counter-offensive honeypots configurations, and observe unique trade-offs, such as longer interactions at the cost of increased detection.

As AI systems gain increasing autonomy and execution capability, the number of discovered security vulnerabilities continues to rise. However, many of these vulnerabilities are not fundamentally novel, but instead reflect recurring classes of weaknesses long observed in prior computing systems. Execution-capable AI agents are effectively unbounded, self-modifying programs that interact extensively with multiple layers of the computing stack. This broad interaction surface imposes a significant security burden on developers, who must reason about and secure complex cross-layer behaviors. Prior research has primarily focused on vulnerabilities in open-source agents and agent frameworks. In contrast, it remains unclear whether proprietary agent systems -- developed under stricter coding standards and formal review processes -- exhibit similar security weaknesses. In this paper, we present findings from two penetration tests conducted in 2025 against proprietary agent products and evaluate whether the security posture of AI agents has improved since these assessments.

Penetration testing is essential to securing modern web infrastructures, yet traditional manual methods struggle to keep pace with their scale and complexity. Large Language Models (LLMs) offer new opportunities for automating these tasks, but existing approaches face two persistent challenges: hallucination of technical entities and insufficient long-term contextual memory. To address these issues, we present APT-Agent, a fully automated LLM-driven penetration testing framework that systematically orchestrates reconnaissance, exploitation, and exfiltration. APT-Agent introduces a hybrid rectification module to recover hallucinated commands and a command-specific memory architecture to preserve operational context across multi-step attack sequences. We evaluate our APT-Agent on Metasploitable 2 against seven vulnerable services spanning web, database, and network protocols. APT-Agent achieves an 84.29% end-to-end exploitation success rate, compared to 48.57% (Script Kiddie) and 18.57% (PentestGPT) under matched conditions. By reducing cognitive burden and minimizing reliance on human intervention, APT-Agent represents a step toward scalable, reliable, and cognitively efficient automation for penetration testing.

We evaluate whether frontier LLMs are ready for cybersecurity through a dual-mode benchmark: white-box function-level vulnerability detection (VulnLLM-R, across C/Java/Python) and black-box web application security testing (five production-style applications with 118 ground-truth vulnerabilities across 20+ CWE families, which we will open-source). We test six frontier models (GPT-5.4, Codex5.3, Claude Opus4.7, Sonnet4.6, Gemini3.1Pro and Gemini3~Flash) and two domain-specialized models across four testing paradigms. Our findings are sobering: (1)~every frontier model produces 10-50% false positive rates in white-box detection, systematically over-predicting vulnerabilities; (2)~in black-box testing, frontier models achieve only 4-8% ground-truth coverage, improving to just 10-19% even with external security tools (Playwright MCP, Burp Suite MCP); (3)~structured penetration-testing methodology encoded in domain-specialized agents raises per-family detection above 50%, demonstrating that methodology, not scale, is the primary lever; and (4)~a domain-specialized defense model achieves the highest precision (0.904) and lowest false positive rate (9.7%) among all models, on a single GPU. We identify the absence of structured security testing traces end-to-end request/response sequences, failure-heavy data, and multi-step attack chains as the fundamental training data bottleneck, and propose self-play security testing as a data generation strategy. Our results make the case for vertical foundation models purpose-built for cybersecurity.

Recent work on LLM-driven autonomous penetration testing reports promising results, but existing systems often combine many architectural, prompting, and tool-integration choices, making it difficult to tell what is gained over a simple agent scaffold. We present cochise, a 597 LOC Python reference harness for autonomous penetration-testing experiments. Cochise connects an LLM-driven agent to a Linux execution host over SSH and supports controlled target environments reachable from that jump host. The prototype implements a separated Planner--Executor architecture in which long-term state is maintained outside the LLM context, while a ReAct-style executor issues commands over SSH and self-corrects based on command outputs. The scenario prompt can be adapted to different target environments. To demonstrate the efficacy of our minimal harness, we evaluate it against a live third-party testbed called Game of Active Directory (GOAD). Alongside the harness, we release replay and analysis tools: (i) cochise-replay for offline visualization of captured runs, (ii) cochise-analyze-alogs and cochise-analyze-graphs for cost, token, duration, and compromise analysis, and (iii) a corpus of JSON trajectory logs from GOAD runs, allowing researchers to study agent behavior without provisioning the 48--64 GB RAM / 190 GB storage testbed themselves. Cochise is intended not as a state-of-the-art pen-testing agent, but as reusable experimental infrastructure for comparing models, agent architectures, and penetration-testing traces.

AI pentesting agents are increasingly credible as offensive security systems, but current benchmarks still provide limited guidance on which will perform best in real-world targets. Existing evaluation protocols assess and optimize for predefined goals such as capture-the-flag, remote code execution, exploit reproduction, or trajectory similarity, in simplified or narrow settings. These tools are valuable for measuring bounded capabilities, yet they do not adequately capture the complexity, open-ended exploration, and strategic decision-making required in realistic pentesting. In this paper, we present a practical evaluation protocol that shifts assessment from task completion to validated vulnerability discovery, allowing evaluation in sufficiently complex targets spanning multiple attack surfaces and vulnerability classes. The protocol combines structured ground-truth with LLM-based semantic matching to identify vulnerabilities, bipartite resolution to score findings under realistic ambiguity, continuous ground-truth maintenance, repeated and cumulative evaluation of stochastic agents, efficiency metrics, and reduced-suite selection for sustainable experimentation. This protocol extends the state of the art by enabling a more realistic, operationally informative comparison of AI pentesting agents. To enable reproducibility, we also release expert-annotated ground truth and code for the proposed evaluation protocol: https://github.com/ethiack/ethibench.

Cyber threats are rapidly increasing, expanding their impact from large-scale enterprises to government services and individual users, making robust security systems increasingly essential. However, a significant shortage of skilled cybersecurity professionals exacerbates this challenge. While recent research has explored automating tasks such as penetration testing using LLM-based agents, existing frameworks often perform poorly due to limited capability in strategy formulation, domain-specific reasoning, and accurate action and tool selection. To overcome these limitations, we propose Pen-Strategist framework, consisting of a novel domain-specific reasoning model that derives pentesting strategies via logical reasoning and a classifier that converts the strategies into actionable steps. First, we construct a reasoning dataset containing logical explanations for both strategy derivation and step selection in pentesting scenarios. We then fine-tune a Qwen-3-14B model for strategy generation using reinforcement learning. Evaluation on the test split of the dataset demonstrates a 87% improvement in strategy derivation performance compared to the baseline. Furthermore, we integrate the fine-tuned Pen-Strategist model into existing automated pentesting frameworks, such as PentestGPT, and evaluate its performance on vulnerable machines, achieving a 47.5% improvement in subtask completion while surpassing the baseline GPT-5. Further experiments on the CTFKnow benchmark show an 18% performance gain over the base model. For step prediction, we train a semantic-based CNN classifier, which outperforms commercial LLMs by 28% and enhances execution stability. Finally, we conduct a user study to qualitatively assess the generated strategies, and Pen-Strategist demonstrates superior performance compared to the Claude-4.6-Sonnet.

Bare-metal operational technology (OT) devices -- especially the microcontrollers running Modbus/TCP and CoAP at the base of industrial control systems -- have remained outside the reach of autonomous security attacks. Prior autonomous pentesting studies target Linux and web systems, whose shells and filesystems are familiar to LLM agents. Bare-metal OT has neither, so agents must reason directly over protocol fields and parser semantics. This requires new action-space designs and runtime controls, and opens new research questions about protocol-level exploit reasoning and its deployment envelope. We present APIOT (Autonomous Purple-teaming for Industrial OT), the first large language model (LLM) framework demonstrating an autonomous attack and remediation of bare-metal OT devices, achieving the full discovery -> exploitation -> patching -> verification cycle without step-by-step human intervention. We implemented and evaluated this framework on Zephyr RTOS firmware across heterogeneous industrial IoT (IIoT) topologies. Through 290 experiment runs spanning five frontier LLMs, three network topologies, two impairment levels, and guided versus unguided conditions, APIOT achieved a mission success rate of 90.0% on the full attack-remediation cycle. We found that the runtime governance layer (which we call an overseer) is a critical engineering variable: without it, agents exhibit systematic degenerate patterns, including repetition loops, missing crash verification, and reconnaissance deadlocks. Together, these findings carry two implications beyond our testbed. Attacker expertise is no longer the binding constraint on bare-metal OT exploitation, and defender threat models must now assume LLM-augmented adversaries capable of executing autonomous discovery-through-remediation cycles against industrial firmware.

Recent research has demonstrated the potential of Large Language Models (LLMs) for autonomous penetration testing, particularly when using cloud-based restricted-weight models. However, reliance on such models introduces security, privacy, and sovereignty concerns, motivating the use of locally hosted open-weight alternatives. Prior work shows that small open-weight models perform poorly on automated Linux privilege escalation, limiting their practical applicability. In this paper, we present a systematic empirical study of whether targeted system-level and prompting interventions can bridge this performance gap. We analyze failure modes of open-weight models in autonomous privilege escalation, map them to established enhancement techniques, and evaluate five concrete interventions (chain-of-thought prompting, retrieval-augmented generation, structured prompts, history compression, and reflective analysis) implemented as extensions to hackingBuddyGPT. Our results show that open-weight models can match or outperform cloud-based baselines such as GPT-4o. With our treatments enabled, Llama3.1 70B exploits 83% of tested vulnerabilities, while smaller models including Llama3.1 8B and Qwen2.5 7B achieve 67% when using guidance. A full-factorial ablation study over all treatment combinations reveals that reflection-based treatments contribute most, while also identifying vulnerability discovery as a remaining bottleneck for local models.

Penetration testing, the practice of simulating cyberattacks to identify vulnerabilities, is a complex sequential decision-making task that is inherently partially observable and features large action spaces. Training reinforcement learning (RL) policies for this domain faces a fundamental bottleneck: existing simulators are too slow to train on realistic network scenarios at scale, resulting in policies that fail to generalize. We present NASimJax, a complete JAX-based reimplementation of the Network Attack Simulator (NASim), achieving up to 100x higher environment throughput than the original simulator. By running the entire training pipeline on hardware accelerators, NASimJax enables experimentation on larger networks under fixed compute budgets that were previously infeasible. We formulate automated penetration testing as a Contextual POMDP and introduce a network generation pipeline that produces structurally diverse and guaranteed-solvable scenarios. Together, these provide a principled basis for studying zero-shot policy generalization. We use the framework to investigate action-space scaling and generalization across networks of up to 40 hosts. We find that Prioritized Level Replay better handles dense training distributions than Domain Randomization, particularly at larger scales, and that training on sparser topologies yields an implicit curriculum that improves out-of-distribution generalization, even on topologies denser than those seen during training. To handle linearly growing action spaces, we propose a two-stage action decomposition (2SAS) that substantially outperforms flat action masking at scale. Finally, we identify a failure mode arising from the interaction between Prioritized Level Replay's episode-reset behaviour and 2SAS's credit assignment structure. NASimJax thus provides a fast, flexible, and realistic platform for advancing RL-based penetration testing.

Penetration testing, the simulation of cyberattacks to identify security vulnerabilities, presents a sequential decision-making problem well-suited for reinforcement learning (RL) automation. Like many applications of RL to real-world problems, partial observability presents a major challenge, as it invalidates the Markov property present in Markov Decision Processes (MDPs). Partially Observable MDPs require history aggregation or belief state estimation to learn successful policies. We investigate stochastic, partially observable penetration testing scenarios over host networks of varying size, aiming to better reflect real-world complexity through more challenging and representative benchmarks. This approach leads to the development of more robust and transferable policies, which are crucial for ensuring reliable performance across diverse and unpredictable real-world environments. Using vanilla Proximal Policy Optimization (PPO) as a baseline, we compare a selection of PPO-based variants designed to mitigate partial observability, including frame-stacking, augmenting observations with historical information, and employing LSTM or TrXL architectures. We conduct a systematic empirical analysis of these algorithms across different host network sizes. We find that this task greatly benefits from history aggregation. Converging up to four times faster than other approaches. Manual inspection of the learned policies by the algorithms reveals clear distinctions and provides insights that go beyond quantitative results.