Objectives: Non-adherence is a major barrier undermining all healing efforts within outpatient programs, resulting in waste of human and social resources. Innovative approaches that could be helpful in combating non-adherence would be based on the latest mobile healthcare technologies, integrated within a carefully planned approach. This study analyzes the factors generating chronically ill outpatient non-adherence and proposes concrete actions through which mobile solutions may address these determinants in a broader context of clinical interventions. The goal of the paper is to explore one of the main dilemmas associated with mobile healthcare interventions: the uncertainty regarding the level of patient involvement and of technology support. Methods: We follow a critical orientation approach in discussing this multifaceted conundrum. We begin by summarizing the latest vision on adherence factors. We then propose six types of interventions through which mobile healthcare solutions could address them. Finally we outline obstacles of m-healthcare solutions in adherence and explore in detail the pivotal dilemma of patient and technology roles. Results: There is no universally optimal solution, and practical conditions depending on patient, disease, treatment, and healthcare system are determining factors in prescribing the level of patient involvement and of technology support. Conclusions: The possible use of mobile healthcare technologies to address outpatient non-adherence would face uncertainties among which the conundrum of patient and technology participation. This work is intended to stimulate further research into the nature of mobile solutions in healthcare, in an endeavour to contribute to improving adherence with minimum patient obtrusiveness.