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This study investigates a technology mentoring program aimed at reducing the digital divide for individuals aged 65 and above. Following a qualitative case study design, we paired 12 teacher candidates with 12 older adults. The philosophical principles of Intergenerational Learning (IGL) and Mezirow's Transformative Learning Theory (TLT) guided this study. The content analysis of 48 reflective portfolios and 20 interviews showed that participants frequently encountered "Disorienting Dilemmas" and engaged in "Self-Examination," which were pivotal in initiating transformative learning experiences. The findings also provided mentoring challenges and key instructional design guidelines for teaching technology to older adults, such as simplifying technology jargon, using visual aids, and addressing physical, cognitive, and psychological barriers.