This contribution is based on a case-study for an ongoing PhD research project on cultural mediators working for an Italian NGO which provides humanitarian aid and medical assistance in complex migration settings. Emergency’s cultural mediators carry out a wide range of tasks, including health and social guidance, information, and cultural mediation. While asked to perform different tasks and flexibly adapt to the changing circumstances, the results of the study show that the NGO’s cultural mediators are faced with major training and ethical challenges. The former concern the lack of training in areas as diverse as language, intercultural mediation, interpreting and translation, ethics, emotions, and vicarious trauma, among others. The latter refer to the cultural mediators’ scarce appreciation of the ethical implications of their actions, as well as their lack of awareness of the difference between the ethics of interpreting and the ethics of humanitarian work when making decisions.