Large language models (LLMs) are typically aligned to a universal set of safety and usage principles intended for broad public acceptability. Yet, real-world applications of LLMs often take place within organizational ecosystems shaped by distinctive corporate policies, regulatory requirements, use cases, brand guidelines, and ethical commitments. This reality highlights the need for rigorous and comprehensive evaluation of LLMs with pluralistic alignment goals, an alignment paradigm that emphasizes adaptability to diverse user values and needs. In this work, we present PLURALISTIC BEHAVIOR SUITE (PBSUITE), a dynamic evaluation suite designed to systematically assess LLMs' capacity to adhere to pluralistic alignment specifications in multi-turn, interactive conversations. PBSUITE consists of (1) a diverse dataset of 300 realistic LLM behavioral policies, grounded in 30 industries; and (2) a dynamic evaluation framework for stress-testing model compliance with custom behavioral specifications under adversarial conditions. Using PBSUITE, We find that leading open- and closed-source LLMs maintain robust adherence to behavioral policies in single-turn settings (less than 4% failure rates), but their compliance weakens substantially in multi-turn adversarial interactions (up to 84% failure rates). These findings highlight that existing model alignment and safety moderation methods fall short in coherently enforcing pluralistic behavioral policies in real-world LLM interactions. Our work contributes both the dataset and analytical framework to support future research toward robust and context-aware pluralistic alignment techniques.