This book focuses on two particular contexts of grandparenting in Newfoundland and Labrador, an island community: grandparents as full time carers and sandwich generation grandparents. We are very much aware of the current global contexts and how grandparents navigate the many different realities and contexts today. Technological, political, economic and social forces have shaped this community as it currently exists. Island communities such as Newfoundland and Labrador are no longer isolated by water masses but have been transformed as part of the global reality and have changed our sense of community. With outmigration of families to other parts of the country and internationally, grandparents and grandparent-grandchild relationships are adapting, in part, by using technology to develop and enhance those relationships through medium such as Skype, “What’s App”, texting, email and so on. In addition grandparents often embed, as part of their travel plans, regular visits to their adult children and grandchildren to maintain those relationships, oftentimes being available to provide extensive levels of care for critical times in the lives of their adult children and, subsequently, their grandchildren. Grandparents are the transmitters of culture, values and knowledge within families and within community.