(1) Background: The communication of hope is complicated, particularly for family caregivers in the context of cancer who struggle to maintain hope for themselves and their loved ones in the face of terminality. In order to understand these complexities, the current study examines the bright and dark sides of how hope is communicated across the cancer journey from the vantage point of bereaved family caregivers; (2) Methods: We analyzed interviews with bereaved family caregivers using qualitative thematic and case oriented strategies to identify patterns in the positive and negative lived experiences when communicating about hope at the end of life; (3) Results: Two overarching patterns of hope emerged. Those who experienced hope as particularized (focused on cure) cited communication about false hope, performing (faking it), and avoidance. Those who transitioned from particularized to generalized hope (hope for a good death) reported acceptance, the communication of hope as social support, prioritizing family, and balancing hope and honesty; (4) Conclusion: Family caregivers face myriad complexities in managing the bright and dark sides of hope. Interventions should encourage concurrent oncological and palliative care, increased perspective-taking among family members, and encourage the transition from particularized to generalized hope.