Qualitative research provides important insights into the experiences and perspectives of older people on end-of-life issues, but such research is methodologically and ethically complex. We offer a set of reflections from six end-of-life care studies conducted with older people in four European countries: Belgium, Germany, the Netherlands, and the United Kingdom. The reflection process was informed by four full-day meetings between the authors and referral to sources including the study interview guides, summary "pen portraits" about key issues encountered in the interviews, and key sections of the interview transcripts. We identified as major challenges accessing people, the introduction of end-of-life issues in an interview, managing emotions, the presence of companions, and reciprocity. Formal ethical review committees rarely take into account these complex issues. We concluded that is it necessary to maintain an ongoing reflexive stance to enhance qualitative research practice in the intersecting fields of aging and end-of-life studies.