Initiating end-of-life (EoL) discussions with patients is often delayed or avoided altogether by healthcare practitioners even in light of imminent death. This continues despite the availability of guidelines and conceptual frameworks on how to communicate prognoses at EoL. We surveyed healthcare practitioners to elicit their exposure to and confidence in EoL discussions and to better understand factors that enable or challenge the initiation of discussions in Australian healthcare settings. Thematic analysis identified that EoL discussions could be emotionally burdensome for healthcare practitioners but were regarded as valuable. Effective communications were challenged by conflict with families and between healthcare practitioners as to appropriate care goal transition, and by prognostic uncertainty. Communication skills appeared to be developed more from experience, and beneficial strategies such as role play and mentoring particularly for younger nurses and doctors were identified. Specific training in EoL communications should target undergraduates and new healthcare practitioners.