Purpose The purpose of the current study was to examine the lexical and pragmatic factors that may contribute to turn-by-turn failures in communication (i.e., miscommunication) that arise regularly in interactive communication. Method Using a corpus from a collaborative dyadic building task, we investigated what differentiated successful from unsuccessful communication and potential factors associated with the choice to provide greater lexical information to a conversation partner. Results We found that more successful dyads' language tended to be associated with greater lexical density, lower ambiguity, and fewer questions. We also found participants were more lexically dense when accepting and integrating a partner's information (i.e., grounding) but were less lexically dense when responding to a question. Finally, an exploratory analysis suggested that dyads tended to spend more lexical effort when responding to an inquiry and used assent language accurately-that is, only when communication was successful. Conclusion Together, the results suggest that miscommunication both emerges and benefits from ambiguous and lexically dense utterances.