The functions of vocal matching have been clarified in territorial songbirds, compositionally stable groups of birds and mammals, and species with multiple alarm or assembly signals. The functions of vocal matching are less well understood in fission/fusion species that are non-territorial, live in groups with variable composition, and lack multiple alarm signals. Here we present the results of interactive playbacks in a fission/fusion parrot species, the orange-fronted conjure (Aratinga canicularis), that provide evidence of vocal matching. A randomly selected loud contact call (chee) per trial was played to passing wild flocks and short-term captives in Costa Rica. Of the trials where subjects interacted, 30% of wild flocks and 21% of captive trials showed significantly linear or curvilinear changes in similarity between the stimulus and response chees over the course of the trial. Surprisingly, both convergent and divergent sequences were observed, and many trials lacking a single trend showed disjunct changes in stimulus-response similarity. These results suggest that chee exchanges prior to flock fusions are not simply an exchange of greetings but are more likely some form of negotiation. This would explain the presence of convergent, divergent, and variable patterns of stimulus-response similarity seen in our experiments.