CIDER: A Dataset of Contextual Disclosure Boundaries for Privacy Preference Alignment

Aligning large language models (LLMs) with human privacy preferences requires capturing individuals' disclosure boundaries beyond general privacy norms. However, a gap remains in eliciting such nuanced preferences to evaluate alignment in realistic settings. We introduce CIDER, a dataset of 14,850 human annotations from 169 users, forming 1,650 contextual disclosure boundary sets across 60 interpersonal communication scenarios involving information sharing that violates privacy norms. Each boundary represents a real user's disclosure decisions over 9 sharing variants in a scenario, for a given communication role and AI-mediated condition. We formulate a task in which models predict a user's disclosure decision from historical boundaries, with varying levels of contextual information. Across 12 open and proprietary models, in-context personalization improves prediction accuracy by up to 11.41 percentage points using only 6 historical examples. Larger models such as GPT-5.4 (with medium reasoning effort) and Claude Sonnet 4.6 are better at leveraging semantic context to understand user-specific, context-dependent disclosure preferences for more accurate predictions, while smaller models tend to rely on structured heuristics based on disclosure granularity and identifiability. Personalization generally improves prediction accuracy, but the improvement is often accompanied by imbalanced shifts in false-positive and false-negative rates across models, with only Claude Sonnet 4.6 achieving balanced improvements in both. Our findings reveal both the promise and limitations of inference-time personalization for privacy preference modeling and position CIDER as a resource for advancing personalized privacy alignment.