The integration of ethics into research with young people in vulnerable life situations is an on-going challenge that cannot be solved through predefined guidelines or fixed standards. In this article, we address the ethical predicaments of keeping in contact with young people in vulnerable life situations through a longer duration of time in order to conduct follow-up interviews. Drawing on cases from two separate studies, the context of the interview situation and the young informant’s general life situation are analyzed in terms of how they influence what is ethically acceptable. While the blurriness of what is appropriate could lead to suggestions for more well-defined ethical guidelines, we argue that the best and most ethical way to deal with this ambiguity is to recognize it and actively address it as both a practical and an academic challenge.