This study explores how older adults use digital health technologies designed to improve medication affordability and accessibility, with a particular focus on multicultural and resource-poor settings. In a trial involving 86 persons aged 60 years and above+, important results were found related to determinants influencing the adoption and effective use of these tools. Older people expressed interest in using digital technologies to support their medication; however, uptake was conditioned by a range of interconnected factors. Digital literacy, clarity of information, and ease of navigation were widely cited as impacting confidence and comfort with digital usage. Language accessibility and cultural familiarity also shaped general satisfaction, with participants reacting positively to technologies that offered clear visuals, simple-to-follow instructions, and logical layouts. The survey was carried out in English, Irish, and Malayalam, so as to be inclusive across language groups and gain a broader understanding of the difficulties and likes within this heterogeneous sample. Hybrid models that blended digital technologies with face-to-face healthcare support—like pharmacist, caregiver, or community support—were particularly valued. Such frameworks provided reassurance, reduced confusion, and enabled ongoing interaction, particularly in those who had less confidence in the use of technology. The integration of human support appeared to increase trust and have a positive impact on medication adherence. The results point to the promise of digital health technologies in lowering medication access and affordability barriers, if designed with accessibility and inclusivity in mind. Incorporating features like intuitive interfaces, culturally tailored design elements, and multilingual capabilities can facilitate usability and promote wider uptake among older adults. To fully realise the potential of such tools, it is important to promote cooperation among healthcare providers, technology creators, and policy makers. Developing solutions that are not just functional but also attuned to the specific needs of ageing populations, particularly those residing in diverse and underserved populations, can facilitate greater equity in access to health services. Enablement programmes that focus on elevating digital literacy and promoting community outreach can also help augment uptake and ensure older adults are able to manage medications effectively in an ever-digitising world.