Background: With the evolution of contemporary occupations mediated by digital technologies (DTs), there is a need for occupational therapists to develop and structure knowledge on how to support older adults’ engagement in occupations and social participation in a digitalised society. Objective: The objective of this study is to explore how tailoring to support older adults’ engagement in DT-mediated occupations could be schematised. Material and methods: The study employed a multiple case study methodology. There were nine cases, with each case involving an older adult undergoing a collaborative process to support engagement in DT-mediated occupations. The collaborative process was initiated through questionnaires, observations, and dialogues. Meetings and tailoring strategies were documented in fieldnotes and memos on tailoring, respectively. Semi-structured interviews concluded data collection. Cross-case synthesis was used in data analysis. Results: The result is a proposed scheme for tailoring to support older adults’ engagement in digital technology-mediated occupations, wherein strategies undertaken in the collaborative processes were synthesised and described. Conclusion and significance: The proposed scheme for tailoring could contribute to occupational therapists’ knowledge on how to support older adults’ engagement in contemporary occupations. Testing the model in various practice settings is recommended in order to enhance occupational therapy practice. Originally included in thesis in manuscript form.