Among the many disruptive effects of a terminal cancer diagnosis in young people is its ability to affect reproductive planning and the opportunity for parenthood. While many reproductive-aged cancer patients receive fertility counseling at diagnosis, ongoing guidance often does not occur during the illness course and associated distress may go unrecognized. Using a case-based framework, this palliative care rounds explores the existential, spiritual, ethical, and logistical challenges that complicate reproductive planning for patients and families as they face a terminal cancer diagnosis. We advocate that palliative care providers should seize currently underrecognized opportunities to screen for distress associated with fertility and reproduction at end of life and utilize an interdisciplinary team approach to provide appropriate support and counseling throughout the illness and bereavement experience.