Despite the primacy of the family in End-of-Life (EoL) decision-making in Asian societies, there is little understanding of how these caregivers come to take on and perform decision-making functions in the family. 12 semi-structured interviews with local caregivers in Singapore were conducted over zoom, with only audio-recordings retained. They were asked to reflect on how they prepared for EoL decisions; moments they felt assured they were making the right choice, and other times where they felt unsure or regretful. Transcripts were coded inductively via reflexive thematic analysis. Three themes emerged from the analysis: (1) factors considered in EoL decision-making; (2) the identification of a lead facilitator and a description of their many duties; and (3) enablers and barriers in EoL decision-making. The results exemplify the local relational dynamics at play in EoL decision-making among patients and their families. Healthcare practitioners should take in consideration its implications on EoL decision-making aids in Singapore.