Blood pressure self-measurement (BPSM) requires patients to follow a range of recommendations in order to be considered reliable for diagnostic use. We investigated currently used BPSM interventions at four medical clinics combined with an online questionnaire targeting BPSM users. We found that the participating healthcare personnel perceived BPSM as a relevant and useful intervention method providing that the recommendations are followed. A total of six challenges were identified: (1) existing devices do not guarantee that the recommendations are followed, (2) healthcare providers cannot verify whether self-monitoring patients follow the recommendations, (3) patients are not aware of all recommendations and the need to follow them, (4) risk of patient induced reporting bias, (5) risk of healthcare provider induced data-transfer bias, and (6) risk of data being registered as belonging to the wrong patient. We conclude that existing BPSM interventions could be significantly affected by user-induced bias resulting in an indeterminable quality of the measurement data. Therefore, we suggest applying context-aware technological support tools to better detect and quantify user errors. This may allow us to develop solutions that could overcome or compensate for such errors in the future.