This interpretative, qualitative study explored residents’ and families’ perspectives on advance care planning (ACP) in long-term care (LTC). Perspectives on when, how, and with whom ACP discussions should be introduced and barriers and solutions to improving ACP engagement were examined. Fifty-one residents and families participated in seven focus groups. The findings revealed that residents and families prioritized caring connections over professional rank when reflecting on staff involvement in ACP. The findings further revealed that the caring and compassionate environment considered to be a critical pre-condition for ACP engagement was more typically enacted at end of life when ACP was no longer an option. Our findings suggest that work practices and organizational structures within LTC play an important role in inhibiting ACP engagement.