With much of the population now online, the field of HCI faces new and pressing issues of how to help people sustain online activity throughout their lives, including through periods of disability. The onset of cognitive impairment later in life affects whether and how individuals are able to stay connected online and manage their digital information. While caregivers play a critical role in the offline lives of adults with cognitive impairments, less is known about how they support and enable online interaction. Using a constructivist grounded theory approach, data from focus groups with caregivers of adults with cognitive impairments reveal four forms of cooperative work caregivers perform in the context of supporting online activity. We find that staying active online is a way of empowering and engaging adults with cognitive impairments, yet this introduces new forms of risk, surrogacy, and cooperative technology use to the already demanding work of caregiving.