Digital technologies have the potential to affect dying and grieving significantly. The role of interactive technologies at End of Life (EoL) is a recently established and quickly growing topic in the CHI community. It is becoming increasingly urgent to create a deep understanding of how to design technologies that address EoL needs – a process termed thanatosensitive design. We propose a workshop that brings together researchers, designers, and entrepreneurs from a variety of disciplines and perspectives around this common theme. The goal of the workshop will be to address the design space, share lessons learned from methodologies and processes, and promote cross-disciplinary knowledge-sharing. Such issues cut across the entire span of work in human-computer interaction, and have a potential impact on all who create a digital footprint.