<p>The aim of this study was to explore healthcare professionals’ (HCPs) experiences of oncology consultations in which a change of treatment is proposed and discussed with patients (and their family caregivers, if present) due to cancer progression. Twenty semi-structured interviews were conducted with HCPs (oncologists, surgeons, and nurses) who regularly disclosed cancer progression. The data were analyzed using a thematic analysis. The member reflections method was used to verify the accuracy of the content of the analysis. Six themes were identified, demonstrating that the disclosure of cancer progression is a process that is not limited to a single consultation. HCPs rely on their knowledge of patients and family caregivers to adapt their communication considering their preferences. Communication skills such as empathy and self-questioning are highly endorsed. The findings highlight the process of breaking bad news and the way in which HCPs deal with consultations to announce the progression of cancer considering criticisms made and proposed improvements. Breaking bad news is a difficult process. Introducing compulsory training as part of the medical curriculum, creating safe, individual listening areas, and encouraging teamwork can help to better support HCPs.</p>