The rise of digital mobile communications has made possible novel research methods that can provide a better understanding of patients’ experience of non-communicable diseases. This study explores the opportunities and challenges in employing “digital diaries” via mobile phones to track the lived experiences of people with hypertension in the Philippines. Following in-depth interviews, 40 hypertensive adults were invited to submit digital diaries over 12 months. Mobile phones were found to be an efficient way of reaching participants, although it was difficult to collect in-depth narratives about their experiences using the medium beyond nominal responses about symptoms and treatment. Possible explanations include the asymptomatic nature of hypertension, which limited the participants’ experiences of the illness, as well as the platform itself, which our mostly-elderly, low-income participants may not be comfortable with. Despite these challenges, “digital diaries” hold potential for the study of other chronic conditions, provided that researchers engage in extensive co-production with participants to understand their preferences. Researchers also need more training in the use of these methods appropriately as part of a suite of methods for capturing the experience of people living with chronic illness.