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Lived experiences of chronic conditions are marked by fluidity and change, which should be considered if care is to be truly patient-centered. Seeking to capture this fluidity, we used digital diaries via mobile phones to communicate with hypertensive patients in the Philippines over approximately 12 months. This paper draws on Strong Structuration Theory to conceptualize the complex array of factors shaping participants’ usage (and non-usage) of the diaries, thereby offering a comprehensive understanding of how the diaries were perceived and used. We draw on qualitative data from 42 participants (73 baseline/follow-up interviews and 37 digital diaries), purposively selected from a larger pool of quantitative participants, as well as existing literature and our own study documents. The Philippines ‘digital divide' presented barriers to the usage of the diaries, stemming from a lack of access and mobile signal especially in socioeconomically marginalized rural areas. Within this context, the sharing of mobile phones both enabled and constricted diary participation. Guided by Strong Structuration Theory, we observed three cycles of structuration evident in participants’ usage of diaries. The first pertained to the frequency and mode of engagement. A low level of engagement was observed, stemming from negative or ambivalent attitudes toward texting and other factors. Conversely, mobile phone ‘top-ups’ enabled participation. Participant usage of the diaries as tools for monitoring hypertension and to request health advice comprise the second and third structuration cycles. These usages contrast with researchers’ intended usage of the diaries and with the original brief given to participants. The conflict between participants’ and researchers’ understanding of the appropriate uses of the diaries represents the dynamic field of position-practice relations, wherein agents are situated and interact, either perpetuating or challenging existing societal structures. Our findings underline the importance of considering macro- and meso-level factors when considering or conducting research using digital diaries.