Microbial cooperative secretions involved in biofilm formation, virulence, or nutrient acquisition provide a collective benefit but are costly for the individual. How these behaviors avoid exploitation by non-producing cheaters is subject of intense research. Here we investigate two cooperative behaviors in medically and environmentally relevant Pseudomonas bacteria: Cell-cell communication, also termed quorum sensing, via diffusible acyl-homoserine lactone signals, and iron acquisition via secreted siderophores. Using a combination of modeling and experimentation, we demonstrate the existence of cheating, and we investigate how the physical and social environment affects cooperator-cheater dynamics. We identify adaptations that sustain cooperation during in vitro evolution and we show that the fitness costs of secretion are nutrient-dependent. Our work has implications for the evolutionary stability of cooperative behavior in pathogenic and non-pathogenic environments, in biotechnological applications, and beyond the microbial realm.