Monitoring of health parameters in non-clinical settings is one strategy to address the increasingly aging population and age-related disabilities and diseases. However, challenges exist when introducing self-monitoring activities in people's everyday life. An active lifestyle can challenge the appropriation of healthcare technologies and people with comorbidity may have diverse but co-existing monitoring needs. In this paper, we seek to understand home-based health monitoring practices to better design and integrate them into people's everyday life. We perform an analysis of socio-technical complexities in home-based healthcare technologies through three case studies of self-monitoring: 1) pre-eclampsia (i.e. pregnancy poisoning), 2) heart conditions, and 3) preventive care. Through the analysis seven themes emerged (people, resources, places, routines, knowledge, control and motivation) that can facilitate the understanding of home-based healthcare activities. We present three modes of self-monitoring use and provide a set of design recommendations for future Ubicomp designs of home-based healthcare technology. Monitoring of health parameters in non-clinical settings is one strategy to address the increasingly aging population and age-related disabilities and diseases. However, challenges exist when introducing self-monitoring activities in people’s everyday life. An active lifestyle can challenge the appropriation of healthcare technologies and people with comorbidity may have diverse but co-existing monitoring needs. In this paper, we seek to understand home-based health monitoring practices to better design and integrate them into people’s everyday life. We perform an analysis of socio-technical complexities in home-based healthcare technologies through three case studies of self-monitoring: 1) pre-eclampsia (i.e. pregnancy poisoning), 2) heart conditions, and 3) preventive care. Through the analysis seven themes emerged (people, resources, places, routines, knowledge, control and motivation) that can facilitate the understanding of home-based healthcare activities. We present three modes of self-monitoring use and provide a set of design recommendations for future Ubicomp designs of home-based healthcare technology.