Wheelchair users, especially those with spinal cord injuries, are at high risk of pressure injuries (PrIs). Prolonged pressure on vulnerable areas, like the ischial tuberosities, is a key cause, and while pressure relief maneuvers are effective, consistent implementation is challenging. Assistive health technologies that promote health prevention by tracking user behaviour show promise in enabling self-monitoring and real-time feedback to improve PrI prevention. However, their success depends on acceptability, including ease of use, psychological comfort, and integration into daily routines. This study aimed to investigate acceptability by gathering insights from wheelchair users and clinicians through interviews and focus groups. Users valued autonomy and preventative strategies such as repositioning and skin care but noted limitations. They saw the technology as beneficial for higher-risk users but emphasised the need for personalisation, discreet alerts, and privacy. Clinicians highlighted its potential to monitor behaviour, provide feedback, and support PrIs prevention but raised concerns about intrusiveness, usability. Both groups emphasised personalisation, simplicity, and affordability. The findings highlight the need for a collaborative, team-based approach, where users and clinicians work together with developers to ensure acceptability and effective implementation. Designing user-centered, clinician-endorsed technologies that adapt to diverse needs is crucial for fostering trust and widespread adoption.