Chronic pain is a burden on an individual, social and economic level. Growing published research outlines various innovative online solutions aimed at addressing this issue, including interactive patient websites. This paper presents expert insights regarding an existing interactive chronic pain website, ‘ONESELF’, operating in Switzerland. Based on their experience, members of the research team involved in the ‘ONESELF’ project were asked to reflect about what they understood to be key considerations salient to designing and implementing such interventions. Thematic analysis uncovered five main themes that these experts used to interpret what worked, when and why in ‘ONESELF’ design and implementation: health literacy, Internet literacy, access to healthcare, adherence and attrition, and health outcomes. These findings may serves as a base to assist Australian health researchers and practitioners working toward developing effective interactive patient websites for people with chronic pain.