End-of-life (EOL) discussions for patients with cancer are a key factor of successful EOL care; however, identifying the optimal timing for these discussions in Japanese home-care settings is difficult. To identify the time at which patients with cancer and their caregivers need EOL discussions, we explored when home-visit nurses start EOL discussions. We interviewed 23 home-visit nurses and analyzed the data using qualitative content analysis. Three themes were derived from the analysis. Participants identified the timing of EOL discussions as being sensitive to patients’ changing health and care needs (increases in patient’s total pain), changes in the family caregiver’s physical or mental condition through daily care (increases in family caregiver distress), and the EOL process that patients follow (trajectory of disease). Developing a tool or in-service educational program that will enable inexperienced or new graduate home-visit nurses to implement EOL discussions at appropriate times is necessary.