The authors examined students' developmental readiness for productively negotiating the disorienting dilemmas and dissonance they experienced during an international service-learning experience. Using a case study methodology, researchers collected data from a diverse group composed of 7 graduate students and 5 undergraduates who participated in a pre-departure course and 3-week immersion in Ecuador, which instructors framed with a critical service-learning pedagogy. Findings emphasize how the complexities of the students' in-country experience sparked disorienting dilemmas and point to the intertwined nature of developmental readiness, dissonance, and emotions during service-learning experiences.