The presence of companions adds complexity to healthcare interactions. Few studies have characterized challenges arising when interactions involve healthcare professionals (HCPs), patients, and companions, or how those challenges are managed. Using conversation analysis, we examined recorded episodes where patients and companions adopt divergent positions on healthcare measures (e.g., walking aids, homecare, medications). We found nine such episodes within a dataset of 37 palliative care consultations with 37 patients, their companions, and ten healthcare practitioners (HCPs)-doctors, physiotherapists and occupational therapists. Palliative care is one of several healthcare domains where companions substantially contribute to care, consultations, and decision making. We propose that, when patients and companions adopt divergent positions, HCPs face a 'dilemma of affiliation' wherein taking a position on the healthcare measure (e.g., recommending it) entails siding with one party, against the other. By examining what happens in the face of patient-companion divergence, we characterize HCPs' strategies and substantiate our proposal that these reflect an underlying dilemma. We show that: HCPs do not immediately take a position on the healthcare measure after patient-companion divergence emerges; and when HCPs take a position later in the consultation, they do so without ostensibly siding with the party who previously supported the healthcare measure. Further, once an HCP takes a position, the party who supports the measure can treat the HCP as an ally. We offer insights and propose implications for: palliative care; the interactional complexities of healthcare decision-making; and consultations in which companions participate.