Most of the risk factors for stroke are modifiable, yet incorporating and sustaining healthy lifestyle habits in daily life that reduce these risk factors is a major challenge. Engaging everyday activities (EEAs) are meaningful activities that are regularly performed that have the potential to contribute to the sustainability of healthy lifestyle habits and reduce risk factors for stroke. The aims of this study were (1) to investigate the feasibility and acceptability of a digitally supported lifestyle program called “Make My Day” (MMD) for people at risk for stroke following a transient ischemic attack, and (2) to describe participants’ stroke risk and lifestyle habits pre- and post-intervention. A multiple case study design using mixed methods was utilized (n = 6). Qualitative and self-reported quantitative data were gathered at baseline, post-intervention, and 12 months post-baseline. The results indicate that MMD can support lifestyle change and self-management for persons at risk for stroke following a TIA. The findings indicate a high acceptability and usability of MMD, as well as a demand for digital support provided via a mobile phone application. Self-management with digital support has the potential to increase participation in EEAs for persons at risk for stroke following a TIA.