The aim of this study was to explore by whom, how, and when discussions about prognosis and end-of-life issues should be initiated with terminally ill patients, and the context in which these issues can be optimally discussed. Focus groups and individual interviews were conducted with 19 palliative care (PC) patients, 24 carers, and 22 PC health professionals (HPs). Participants had disparate views regarding by whom and when such discussions should be initiated, although a similar range of perspectives was expressed by all participant groups. Four main approaches were identified: wait for the patient/carer to raise the topic; HPs to offer all PC patients and their carers the opportunity to discuss the future (preferred by the majority of participants); HPs to initiate the discussion when the patient/family need to know; or HPs to initiate the discussion when the patient/family seem ready. Four themes emerged regarding the optimal context of the discussion: importance of the relationship with HP, clarifying the patient/carers' understanding and how much detail they want to know, negotiating who should be present during the discussion, and who should deliver the information. Initiating prognostic discussions with terminally ill patients requires considerable skill and sensitivity. Communication skills training for HPs may be required to optimize such discussions.