Background:  Internet-based interventions are increasingly used for chronic pain and migraine, yet little is known about how different forms of content shape participants’ engagement, understanding, and learning. Even though patients are the main agents of change in digital treatment, few studies have examined differences between explicit, psychoeducational formats and experiential, metaphor-rich approaches in terms of their impact on engagement and learning. Understanding more about the content and learning processes may help optimise design and delivery, and improve relevance, adherence, and outcomes. Aim: This study explored how participants learned and engaged in two internet-based pain interventions, and how content and format shaped these experiences: one self-guided psychoeducational program for chronic pain and one therapist-supported CBT/ACT program for migraine. Method: Fourteen participants (self-guided: n = 8; therapist-supported: n = 6) were interviewed. Data were analysed using reflexive thematic analysis within a critical realist framework. Results: Two overarching themes were developed. The first concerned the importance of clarity: explicit explanations, structure, and visual or metaphorical material helped participants understand, stay motivated, and engage. An experiential sense of clarity, combining explicit understanding with emotional engagement and coherence, appeared relevant. The second theme was the balance between autonomy and guidance. Preferences varied, but participants stressed the need to grasp the rationale and to receive flexible support for sustained involvement. Conclusions: Clarity seems to be central to engagement and learning in digital pain interventions. Combining explicit information with visual and metaphorical material in a flexible, structured framework may strengthen both cognitive and experiential learning, enhance motivation, and support adherence.