The 'baby boomers' are those who were born in the two decades since the end of the Second World War and in their diverse ways have grappled with the evolution of computers, the Internet and mobile phone. The market demand of those born from the 1990's onwards has driven these technologies in further unforeseen directions. This paper framed in the context of generational and technological change and is based on the observation that mobile phone technology will become the 'preferred platform' for enabling an aging population to live independently for much longer in their own home. The paper will draw upon recent research into the understanding of the diverse attitudes and backgrounds of older people that informs understanding of their likely propensity for adoption of these technologies. The paper will also scan technology development and critique the supply side products designed to meet the perceived needs of older people such as emergency pendants and mobile phones with big buttons. This analysis of both supply and demand side has informed the development of a communications service product called Assure ConnectTM that can provide an added service feature to any phone system to provide families and groups a communications capability to better support each other. The research approach is akin to 'reading tea leaves'.