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Background: Appropriate timing to initiate advance care planning is difficult, especially for individuals with non-malignant disease in community settings. Aim: To identify the optimal moment for, and reasons to initiate advance care planning in different illness trajectories. Design and methods: A health records survey study; health records were presented to 83 GPs with request to indicate and substantiate what they considered optimal advance care planning timing within the 2 years before death. We used quantitative and qualitative analyses. Setting and patients: We selected and anonymized 90 health records of patients who died with cancer, organ failure or multimorbidity, from a regional primary care registration database in the Netherlands. Results: The median optimal advance care planning timing according to the GPs was 228 days before death (interquartile range 392). This moment was closer to death for cancer (87.5 days before death, IQR 302) than for organ failure (266 days before death, IQR 401) and multimorbidity (290 days before death, IQR 389) (p < 0.001). The most frequently mentioned reason for cancer was "receiving a diagnosis" (21.5%), for organ failure it was "after a period of illness" (14.7%), and for multimorbidity it was "age" and "patients" expressed wishes or reflections' (both 12.0%). Conclusion: The optimal advance care planning timing and reasons to initiate advance care planning indicated by GPs differ between patients with cancer and other illnesses, and they also differ between GPs. This suggests that "the" optimal timing for ACP should be seen as a "window of opportunity" for the different disease trajectories. [ABSTRACT FROM AUTHOR]