Design of mobile, personalised healthcare information systems facilitate a paradigm shift in management of chronic conditions. They provide an infrastructure for creating personalised treatment plans that are evidence based. This is especially important in chronic pain, which is a long-term condition and requires self-management by the patient. In this paper, we use a mobile accessible, web based system to collect daily reports on chronic low back pain. Based on this data a pain trajectory is generated to provide a report for patients to track their pain. We present an empirical study exploring the experiences of the participants, the usability, and issues that encompass frequent data collection using such systems in chronic low back pain.