As communication technologies continue to rapidly evolve, older adults face challenges to access systems and devices, which may increase their social isolation. Our project investigates the design of a digital pen and paper-based communication system that allows users to connect to their family and friends' e-mail inboxes. Given the unique needs of older adults, we opted for a participatory design approach, prototyping the system with 22 older adults through a series of design workshops in two locations. Four individuals used our resulting system over a period of two weeks. Based on their feedback and a review of design workshops, we are currently in the process of refining our interface and preparing for a larger deployment study.