Background: Pregnant diabetic patients are often required to self- measure their blood pressure in the waiting room before consulta- tion. Currently used blood pressure devices do not guarantee valid measurements when used unsupervised. This could lead to misdi- agnosis and treatment error. The aim of this study was to investigate current use of blood pressure self-measurement in the waiting room in order to identify challenges that could influence the resulting data quality. Also, we wanted to investigate the potential for addressing these challenges with e-health and telemedicine technology. Subjects and Methods: We observed 81 pregnant diabetics’ ability to correctly self-measure in the waiting room during a 4-week observational descriptive study. Specifically, we investigated the level of patient adherence to six recommendations with which patients are in- structed to comply in order to obtain a reliable blood pressure reading. Results: We found that the patients did not adhere to given instructions when performing blood pressure self-measurement in the waiting room. None of the 81 patients adhered to all six inves- tigated recommendations, while around a quarter adhered to five out of six of the recommendations. The majority followed four or fewer of the recommendations. Conclusions: Results indicate that unsuper- vised self-measurement of blood pressure is not a reliable method. Thus, there is a need for increased staff presence and patient training or, alternatively, for introducing improved technology support. This could include context-aware patient adherence aids and clinical decision support systems for automatically validating self-measured data based on e-health and telemedicine technology.