Systems and methods are configured for predictive prompt generation for an interaction between a party and an automated prompt system. In various embodiments, metadata is received on the interaction and provided as input to a multi-label predictive model to generate interaction probabilities for a plurality of prompt information data objects. Each probability generated by the predictive model provides a likelihood a particular information data object needs to be provided to the first party during the interaction. Accordingly, one or more of the prompt information data objects are identified based on the probability of each piece found in the one or more prompt information data objects that satisfy a set threshold and one or more notifications are provided so that the automated prompt system provides at least one of the prompt information data objects to the first party during the interaction.