Innovative technologies offer potential benefits for the health and care needs of an ageing population, but the processes by which these innovations are developed and implemented are not well understood. As part of a Canadian research network focused on ageing and technology, we explored how technologies currently being developed to support older adults and their caregivers fare through the processes of innovation. We conducted a multiple case study focused on development of four technology products. Interviews were conducted with project members (n = 8) during site visits to the locations of the four cases, as well as with other key informants (n = 12). Directed coding, guided by the Accelerating Diffusion of Proven Technologies for Older Adults (ADOPT) model was used to analyse the data. Findings illustrate the complexities of innovation processes, including the challenges in developing a business case as well as benefits of a collaborative network.