The rapid improvement of LLMs has made distinguishing AI-generated text from human writing a pressing problem. This challenge is further amplified by paraphrasing tools designed to make machine-generated text appear more "human". We study how access to human writing samples can be used to strategically paraphrase machine-generated responses toward the human distribution. Under a multi-sample setting with human and machine responses to the same prompts, we show that repeated paraphrasing moves the machine distribution toward the empirical human distribution under simple mixing and stability conditions. Our results derive an explicit convergence rate, extend the analysis to a finite-sample setting, and characterize how the required number of human samples and paraphrasing rounds scale with the desired error.
Production LLM applications stack several defense families -- refusal-phrase filters, token-budget controls, model allowlists, rate limits, tool-registry authentication -- yet existing breach-and-attack-simulation (BAS) benchmarks report a single aggregate coverage number, hiding which family closes which threat. We measure attribution. We add four OWASP-LLM-Top-10-aware agents to a 21-agent baseline scanner and target a lattice of four synthetic LLM endpoints: $L_0$ (no defenses), $L_1$ (refusal-only), $L_2$ (budget-only), and $L_3$ (full stack). $L_1$ and $L_2$ are sibling single-axis ablations, not subsets of each other; $L_3$ is their union plus tool-registry authentication and credential scrubbing. Across $N=10$ replications, the per-OWASP finding count is clean: refusal alone removes all LLM01 (jailbreak) and LLM07 (system-prompt leakage) findings; budget alone removes all LLM02 (sensitive-info disclosure) and LLM10 (unbounded consumption) findings by terminating multi-step sequences; LLM06 (excessive agency) requires the full stack. We probe brittleness under paraphrasing: with 300 Gemini-generated paraphrases ($K=5$ over a 60-template brittleness corpus), $L_1$ refusal block rate falls 15 pp on LLM01 and 25 pp on LLM07. A fifth target, $L_4$-real, swaps the stub backend for Gemini-2.5-flash behind the same $L_3$ regex and matches $L_1$ exactly, indicating no measurable alignment contribution beyond the regex (not a general claim about alignment). Budget controls show no drop (0 pp once the rate-limit floor is factored out). A refusal whitelist that clears a static benchmark can be defeated by an LLM-driven paraphraser without changing attack intent; a budget control resists the same mutation.