Abstract Purpose Various personal monitoring technologies have been introduced for supporting regular physical activity, which is of critical importance in reducing the risks of several chronic diseases. Recent studies suggest that combining multiple modes of delivery, such as text messages and mobile monitoring devices with web applications, holds potential for effectively supporting physical exercise. Of particular interest is how the functionality and content of these systems should be distributed across the different modes for successful outcomes. Objectives The aim of this study was to: (a) investigate how users incorporate a system employing two modes of delivery – a wearable heart rate monitor and a web service – into their training and (b) to analyze benefits and limitations in personal exercise monitoring and how they relate to the different modes in use. Methods A qualitative field study employing diaries and semi-structured interviews was carried out with 30 participants who used a heart rate monitoring system comprising a wearable heart rate monitor, Polar FT60 and a web service, Polar Personal Trainer for a period of 21 days. The data were systematically analyzed to identify specific benefits and limitations associated with the system characteristics and modes as perceived by the end-users. Results The benefits include supporting exploratory learning, controlling target behavior, rectifying behaviors, motivation and logging support. The limitations are associated with information for validating the system, virtual coaching, task-technology fit, data integrity and privacy concerns. Mobile interfaces enable exploratory learning and controlling of target behaviors in situ, while web services can effectively support users’ need for cognition within the early stages of adoption and long-term training with intelligent coaching functionality. Conclusions This study explains several benefits and limitations in personal exercise monitoring. These can be addressed with crossmedial design, i.e., strategic distribution of functionality and content across modes within the system. Our findings suggest that personal exercise monitoring systems may be improved by more systematically combining mobile and web-based functionality.