In the context of an oncologic disease delivering bad news always represents a challenge, but a diagnosis such as a retinoblastoma can raise additional problems. Retinoblastoma (RB) is a malignant tumor of the embryonic neural retina network affecting children. It can be either hereditary or sporadic; in advanced stages, it can invade the optic nerve. Approximately 90% of cases are sporadic, with no RB antecedents in the family. Familial RB is present when there is a positive history in one of the child’s parents. Though it can affect the quality of life, the literature usually describes an excellent prognosis for RB patients if the disease is discovered and treated in time. Approaching RB cases must therefore be a holistic, complex, and a multidisciplinary endeavor to ensure the comfort and a better quality of life for the patients and their families. Communication with the family plays a crucial role in achieving this comfort during the entire treatment process. This paper aims is to present three cases diagnosed with RB in our clinic, the ethical dilemmas, and the communication issues that arose while working on these cases and how the different approaches influenced the treatment’s outcome.