Objective: To explore family caregivers' emotional experiences while caring for patients with advanced cancer and navigating distressing information, awareness of dying, and difficult decisions. Methods: Qualitative descriptive study of semi-structured interviews with 92 bereaved caregivers of patients with advanced cancer. Interviews explored caregivers' experiences as patients transitioned out of active cancer treatment and neared the end of life. Results: Included in caregivers' characterization of this transition time were three particularly emotionally charged experiences. The first occurred when caregivers felt jolted into awareness that patients were dying.They were startled to realize that patients would die sooner than expected; some expressed frustration that they had not been adequately warned. In the second, caregivers felt conflicted when involved in decisions that pitted patients' preferences against what caregivers felt patients needed, resulting in ambivalence, guilt, and grief. Thirdly, caregivers who felt they did their best for patients expressed fulfillment and gratitude. Conclusion: Caregivers of patients with advanced cancer face unique, emotionally charged experiences that can lead to distress and affect care at the end of life. Practice Implications: Awareness of these situations may help oncology teams to provide sufficient guidance and support, partner with caregivers to clarify patients' needs, and deliver higher quality care.