As digital inclusion becomes a growing indicator of wellbeing in later life, the ability to understand older adults’ preferences for information and communication technologies (ICTs) and develop strategies to support their digital literacy is critical. The barriers older adults face include their perceived ICT risks and capacity to learn. Complexities, including ICT environmental stressors and societal norms, may require concerted engagement with older adults to achieve higher digital literacy competencies. This article describes the results of a series of co-design workshops to develop strategies for increased ICT competencies and reduced perceived risks among older adults. Engaging older Australians in three in-person workshops (each workshop consisting of 15 people), this study adapted the “Scenario Personarrative Method” to illustrate the experiences of people with technology and rich pictures of the strategies seniors employ. Through the enrichment of low-to-high-digital-literacy personas and mapping workshop participant responses to several scenarios, the workshops contextualized the different opportunities and barriers seniors may face, offering a useful approach toward collaborative strategy development. We argued that in using co-designed persona methods, scholars can develop more nuance in generating ICT risk strategies that are built with and for older adults. By allowing risks to be contextualized through this approach, we illustrated the novelty of adapting the Scenario Personarrative Method to provide insights into perceived barriers and to build skills, motivations, and strategies toward enhancing digital literacy.