The amino acid tryptophan (Trp) is precursor of the neurotransmitter serotonin. Trp supplementation or other forms of serotonergic enhancement generally promote pro-social behavior, decreasing aggression and also feeding in different animals. However, past research has been conducted in confined spaces, and there is little work in naturalistic conditions where animals move and associate more freely. We gave a Trp-enriched diet to a free-flying flock of common waxbills (Estrilda astrild) in semi-natural conditions, and monitored group foraging, aggressions during feeding and the social network. Contrary to expectations, aggressiveness and feeding increased during Trp supplementation. Consistent with the prediction of increased social associations, foraging groups became larger and individuals joined more foraging groups, but these changes appear driven by increased appetite during Trp treatment. Also, the mean strength of associations in the social network did not change. Overall, Trp supplementation affected group behavior in this free-flying flock, but mostly in directions unanticipated based on research conducted in small spaces. To harmonize our results with those found in small confined spaces, we hypothesise that free-flying birds have energetic requirements not experienced in lab-housed individuals, which may impact social behaviour and responses to Trp.