Human behavioral choices can reveal intrinsic and extrinsic decision-influencing factors. We investigate the inference of choice priors in situations of referential ambiguity. In particular, we use the scenario of signaling games and investigate to which extent study participants profit from actively engaging in the task. Previous work has revealed that speakers are able to infer listeners’ choice priors upon observing ambiguity resolution. However, it was also shown that only a small group of participants was able to strategically construct ambiguous situations to create learning opportunities. This paper sets to address how prior inference unfolds in more complex learning scenarios. In Experiment 1, we examine whether participants accumulate evidence about inferred choice priors across a series of four consecutive trials. Despite the intuitive simplicity of the task, information integration turns out to be only partially successful. Integration errors result from a variety of sources, including transitivity failure and recency bias. In Experiment 2, we investigate how the ability to actively construct learning scenarios affects the success of prior inference and whether the iterative settings improve the ability to choose utterances strategically. The results suggest that full task engagement and explicit access to the reasoning pipeline facilitates the invocation of optimal utterance choices as well as the accurate inference of listeners’ choice priors.