Age estimation systems are increasingly deployed as gatekeepers for age-restricted online content, yet their robustness to cosmetic modifications has not been systematically evaluated. We investigate whether simple, household-accessible cosmetic changes, including beards, grey hair, makeup, and simulated wrinkles, can cause AI age estimators to classify minors as adults. To study this threat at scale without ethical concerns, we simulate these physical attacks on 329 facial images of individuals aged 10 to 21 using a VLM image editor (Gemini 2.5 Flash Image). We then evaluate eight models from our prior benchmark: five specialized architectures (MiVOLO, Custom-Best, Herosan, MiViaLab, DEX) and three vision-language models (Gemini 3 Flash, Gemini 2.5 Flash, GPT-5-Nano). We introduce the Attack Conversion Rate (ACR), defined as the fraction of images predicted as minor at baseline that flip to adult after attack, a population-agnostic metric that does not depend on the ratio of minors to adults in the test set. Our results reveal that a synthetic beard alone achieves 28 to 69 percent ACR across all eight models; combining all four attacks shifts predicted age by +7.7 years on average across all 329 subjects and reaches up to 83 percent ACR; and vision-language models exhibit lower ACR (59 to 71 percent) than specialized models (63 to 83 percent) under the full attack, although the ACR ranges overlap and the difference is not statistically tested. These findings highlight a critical vulnerability in deployed age-verification pipelines and call for adversarial robustness evaluation as a mandatory criterion for model selection.

As large language models (LLMs) become integral to multi-agent systems, new privacy risks emerge that extend beyond memorization, direct inference, or single-turn evaluations. In particular, seemingly innocuous responses, when composed across interactions, can cumulatively enable adversaries to recover sensitive information, a phenomenon we term compositional privacy leakage. We present the first systematic study of such compositional privacy leaks and possible mitigation methods in multi-agent LLM systems. First, we develop a framework that models how auxiliary knowledge and agent interactions jointly amplify privacy risks, even when each response is benign in isolation. Next, to mitigate this, we propose and evaluate two defense strategies: (1) Theory-of-Mind defense (ToM), where defender agents infer a questioner's intent by anticipating how their outputs may be exploited by adversaries, and (2) Collaborative Consensus Defense (CoDef), where responder agents collaborate with peers who vote based on a shared aggregated state to restrict sensitive information spread. Crucially, we balance our evaluation across compositions that expose sensitive information and compositions that yield benign inferences. Our experiments quantify how these defense strategies differ in balancing the privacy-utility trade-off. We find that while chain-of-thought alone offers limited protection to leakage (~39% sensitive blocking rate), our ToM defense substantially improves sensitive query blocking (up to 97%) but can reduce benign task success. CoDef achieves the best balance, yielding the highest Balanced Outcome (79.8%), highlighting the benefit of combining explicit reasoning with defender collaboration. Together, our results expose a new class of risks in collaborative LLM deployments and provide actionable insights for designing safeguards against compositional, context-driven privacy leakage.

Studying the responses of large language models (LLMs) to loopholes presents a two-fold opportunity. First, it affords us a lens through which to examine ambiguity and pragmatics in LLMs, since exploiting a loophole requires identifying ambiguity and performing sophisticated pragmatic reasoning. Second, loopholes pose an interesting and novel alignment problem where the model is presented with conflicting goals and can exploit ambiguities to its own advantage. To address these questions, we design scenarios where LLMs are given a goal and an ambiguous user instruction in conflict with the goal, with scenarios covering scalar implicature, structural ambiguities, and power dynamics. We then measure different models' abilities to exploit loopholes to satisfy their given goals as opposed to the goals of the user. We find that both closed-source and stronger open-source models can identify ambiguities and exploit their resulting loopholes, presenting a potential AI safety risk. Our analysis indicates that models which exploit loopholes explicitly identify and reason about both ambiguity and conflicting goals.