Large language models (LLMs) are increasingly deployed in real-world communication settings, yet their ability to resolve context-dependent ambiguity remains underexplored. In this work, we present EMODIS, a new benchmark for evaluating LLMs’ capacity to interpret ambiguous emoji expressions under minimal but contrastive textual contexts. Each instance in EMODIS comprises an ambiguous sentence containing an emoji, two distinct disambiguating contexts that lead to divergent interpretations, and a specific question that requires contextual reasoning. We evaluate both open-source and API-based LLMs, and find that even the strongest models frequently fail to distinguish meanings when only subtle contextual cues are present. Further analysis reveals systematic biases toward dominant interpretations and limited sensitivity to pragmatic contrast. EMODIS provides a rigorous testbed for assessing contextual disambiguation, and highlights the gap between human-level and model-level semantic reasoning.