Large language models (LLMs) are now deployed at unprecedented scale, assisting millions of users in daily tasks. However, the risk of these models assisting unlawful activities remains underexplored. In this study, we define this high-risk behavior as complicit facilitation - the provision of guidance or support that enables illicit user instructions - and present four empirical studies that assess its prevalence in widely deployed LLMs. Using real-world legal cases and established legal frameworks, we construct an evaluation benchmark spanning 269 illicit scenarios and 50 illicit intents to assess LLMs' complicit facilitation behavior. Our findings reveal widespread LLM susceptibility to complicit facilitation, with GPT-4o providing illicit assistance in nearly half of tested cases. Moreover, LLMs exhibit deficient performance in delivering credible legal warnings and positive guidance. Further analysis uncovers substantial safety variation across socio-legal contexts. On the legal side, we observe heightened complicity for crimes against societal interests, non-extreme but frequently occurring violations, and malicious intents driven by subjective motives or deceptive justifications. On the social side, we identify demographic disparities that reveal concerning complicit patterns towards marginalized and disadvantaged groups, with older adults, racial minorities, and individuals in lower-prestige occupations disproportionately more likely to receive unlawful guidance. Analysis of model reasoning traces suggests that model-perceived stereotypes, characterized along warmth and competence, are associated with the model's complicit behavior. Finally, we demonstrate that existing safety alignment strategies are insufficient and may even exacerbate complicit behavior.