This article contributes to a growing literature that takes a more nuanced approach to exploring the complexities of relationships and negotiations with gatekeepers. Using our study of young people living with a parent at the end of life as a 'critical case' of sensitive qualitative research, we discuss how far from being a smooth, linear process, participant recruitment was experienced as a series of overlapping challenges, characterised here as 'wheels within wheels'. Each component of this multi-faceted process relied on identifying and engaging with key practitioners who acted as gatekeepers. We discuss how researcher and gatekeeper positionality influenced the outcome of negotiations with gatekeepers, and highlight potential implications for young people in exigent sets of circumstances. If the routes 'in' to access young people are difficult, then this also raises questions about routes 'out' for young people and their access to support when living through challenging times.