Background Chronic musculoskeletal pain (CMP) is the most common self-reported chronic pain condition. Current treatment for CMP is limited. Methods This was a two-phase study. In Phase 1, three auricular point acupressure (APA)-naïve participants were recruited to explore their experiences of APA and a smartphone app was developed based on their feedback. In Phase 2, a prospective longitudinal study was used to examine the effectiveness of the smartphone app to self-manage CMP. Results Phase 1 resulted in the successful development of the APA smartphone app. In Phase 2, after four weeks of APA, participants reported reduced pain intensity (30%), pain interference (35%), and disability (40%), as well as improved physical function (47%). The mean score for the participants’ perception of treatment efficacy was 4.94 (SD = 2.08, scale of 0–7) indicating that approximately 70% of participants rated global improvements with noticeable changes. The majority (88%, n = 22) of the participants were satisfied with the treatment: 32% [8] were very satisfied and 56% [n = 14] were somewhat satisfied. The average frequency of pressing APA seeds per day was 2.93 times (SD = 2.27, range 0–10) and 1.60 minutes per time (SD = 2.64, range 0–10); the participants were able to adhere to the suggested pressing time per day, although they only pressed the ear points about 53% of the suggested time. Conclusion It is feasible for individuals to learn APA from the smartphone app and successfully self-administer APA to manage their pain. Participants found the app useful and were satisfied with the information provided through the app.