This chapter examines the role of information and communication technologies (ICTs) in family life from the perspective of older adults, and whether ICT use is helping to maintain and strengthen social ties within and across generations. Drawing on networked individualism as a conceptual and analytical model, it investigates social and network transitions affecting families and communities since the 1990s. In-depth interviews conducted in 2013–2014 with older adults from East York, Toronto, show that most of them rely more on email and less on social media and video chat. Most importantly, they still prefer spending time in person. The chapter also considers how the so-called Triple Revolution in how society operates has created opportunities for a transition to networked individualism that affects family interactions. Finally, it discusses three areas where ICTs have been integrated into family life: practices of connectivity, maintaining family ties near and far, and feelings of connectedness.