People generate vast quantities of digital information as a product of their interactions with digital systems and with other people. As this information grows in scale and becomes increasingly distributed through different accounts, identities, and services, researchers have studied how best to develop tools to help people manage and derive meaning from it. Looking forward, these issues acquire new complexity when considered in the context of the information that is generated across one’s life or across generations. The long-term lens of a multigenerational timeframe elicits new questions about how people can engage with these heterogeneous collections of information and how future generations will manage and make sense of the information left behind by their ancestors. My prior work has examined how people perceive the role that systems will play in the long-term availability, management, and interpretation of digital information. This work demonstrates that while people certainly ascribe meaning to aspects of their digital information and believe that there is value held in their largely uncurated digital materials, it is not clear how or if that digital information will be transmitted, interpreted, or maintained by future generations. Furthermore, this work illustrates that there is a tension between the use of digital systems as ways of archiving content and sharing aspects of one’s life, and an uncertainty about the long term availability of the information shared through those services. Finally, this work illustrates the ways in which existing systems do not meet the needs of current users who are developing archives of their own digital information nor of future users who might try and derive meaning from information left behind by other people. Building on that earlier work, my dissertation work investigates how we can develop systems that foster engagement with lifetimes or generations of digital information in ways that are sensitive to how people define and communicate their identity and how they reflect on their life and experiences. For this work, I built a website that uses people’s Facebook data to ask them to reflect on the ways their life has changed over time. Participants’ experiences using this website illustrate the types of information that are and are not captured by digital systems. In addition, this work highlights the ways in which people engage with memories, artifacts, and experiences of people who have passed away and considers how digital systems and information can support those practices. I also interviewed participants about their experiences researching their family history, the ways in which they remember people who’ve passed away, and unresolved questions they have about the past. The findings from this aspect of the work contribute a better understanding of how digital systems, and the digital information people create over the course of their lives, intersect with the processes of death, dying, and remembrance.