Quantifying Frontier LLM Capabilities for Container Sandbox Escape

Exploitation is not a binary event. It is a ladder of acquiring progressive capabilities, from executing a single buggy line of code to taking full control of the target. However, existing LLM security benchmarks treat a crash as exploitation success. That single binary outcome collapses the hard parts of exploitation: the transition from triggering a bug to constructing reusable primitives and control. We present ExploitBench, a capability-graded benchmark that decomposes exploitation into 16 measurable flags, from coverage and crash through sandbox primitives, arbitrary read/write, control-flow hijack, and arbitrary code execution. Each capability is verified by a deterministic oracle that uses a per-run randomized challenge-response for primitives, differential execution against ground-truth binaries to measure progress, and a signal-handler proof for code execution. We instantiate ExploitBench on 41 V8 bugs because V8 is both widely deployed and exploitation-hardened. We report three arms: <model,env> as the primary measurement of model-environment capability, <model,env, adaptive coaching> as a secondary arm that adds adaptive coaching to test whether targeted feedback shifts outcomes, and <model,env,harness> as an ablation that swaps in the model's native CLI to check whether vendor-side optimizations increase exploitation capabilities. Our results show a sharp capability split between publicly deployed frontier models and the private frontier. Across the 8 publicly deployed models tested, reaching the vulnerable code and triggering a crash is routine, but arbitrary code execution is not. The private model shows arbitrary code execution on approximately half. Overall, results suggest that exploit construction against hardened targets is an emerging frontier capability.

Code-capable large language model (LLM) agents are embedded in software engineering workflows where they can read, write, and execute code, raising "jailbreak" stakes beyond text-only settings. Prior evaluations emphasize refusal or harmful-text detection, leaving open whether agents compile and run malicious programs. We present JAWS-Bench (Jailbreaks Across WorkSpaces), a benchmark spanning three escalating workspace regimes mirroring attacker capability: empty (JAWS-0), single-file (JAWS-1), and multi-file (JAWS-M). We pair it with a hierarchical, executable-aware Judge Framework that tests (i) compliance, (ii) attack success, (iii) syntactic correctness, and (iv) runtime executability to measure deployable harm. Across seven LLM backends from five families, prompt-only attacks in JAWS-0 achieve 61% compliance; 58% are harmful, 52% parse, and 27% run end-to-end. In JAWS-1, compliance reaches ~100% for stronger models with a mean ASR (Attack Success Rate) ~71%; JAWS-M raises mean ASR to ~75%, with 32% runnable attack code. Wrapping an LLM in an agent increases ASR by 1.6$\times$, by overturning initial refusals during planning and tool use. Additional evaluations with SWE-Agent and OpenAI Codex exhibit similar trends, indicating that JAWS-Bench can be reused across multiple agent frameworks. Category analyses identify which attack classes are most vulnerable and deployable, motivating execution-aware defenses and refusal-preserving agent designs.

Tool-using language-model agents introduce security failures that go beyond unsafe text: they can disclose protected objects, write persistent memory, send messages, modify databases, or trigger harmful code and tool effects. Existing evaluations often collapse these stages into a single attack success rate, making it difficult to tell whether a model merely agreed with an attacker or actually produced observable harm. We introduce SafeClawBench, a staged benchmark for tool-using agent security with 600 controlled adversarial tasks across six attack families: direct and indirect prompt injection, tool-return injection, memory poisoning, memory extraction, and ambiguity-driven unsafe inference. SafeClawBench reports three separate endpoints: semantic attack acceptance, audit-visible harm evidence, and sandbox-observed tool/state harm. Evaluating five agent endpoints under four prompt-level policies, we find that these endpoints capture different failure modes. Without additional prompt protection, semantic failure rates vary widely across models, from 9.0% to 44.2%. Audited harm evidence is narrower than semantic failure, and under a separate executable protocol some matched task identities produce sandbox harm despite passing the Semantic Core call: in a 12,000-row matched analysis, 291 of 347 observed sandbox harms occur in rows that pass the semantic check. Prompt policies change endpoint outcomes, but their effects depend on both model and protocol. SafeClawBench provides a reproducible framework for comparing agent models and prompt-policy conditions without conflating textual compliance, evidence-supported harm, and executable state changes. The open-source dataset is available at https://huggingface.co/datasets/sairights/safeclawbench.