With the increasing size and complexity of personal information and data landscapes, there is a need for guidance and support in the appropriate management of a deceased person’s postmortem privacy and digital legacy. However, most people engage poorly with existing mechanisms for specifying and planning for access and suitable usage of their own data. We report on two studies exploring the ways in which contextual factors such as the accessor and the data type may affect the appropriateness of personal data flows differently during life and after death. Our findings indicate that suitable data access after death is highly individual and contextual, with differences in appropriateness between during-life and after-death data flows significantly affected by the accessor and the data type in question. We identify that ambiguous accessor motivation, failure to communicate intent, changing temporal context and latent data values further complicate the act of digital legacy planning. Our findings also provide further evidence for the existence of a postmortem privacy paradox in which reported user behaviors do not reflect intent. With this in mind, we offer design recommendations for the integration of digital legacy planning functionality within Personal Information Management (PIM) and Group Information Management (GIM) systems.