Individuals with spinal cord injury (SCI) need to perform numerous self-care behaviors, some very frequently. Pressure reliefs (PRs), which prevent life-threatening pressure ulcers (PUs), are one such behavior. We conducted a qualitative study with seven individuals with severe SCI—who depend on power wheelchairs—to explore their current PR behavior and the potential for technology to facilitate PR adherence. While our participants were highly motivated to perform PRs because of prior PUs, we found that their understanding of how and when to perform a PR differed by individual, and that while they sometimes forgot to perform PR, in other cases contextual factors made it difficult to perform a PR. Our findings provide insight into the complexity of this design space, identify design considerations for designing technology to facilitate these behaviors, and demonstrate the opportunity for personal informatics to be more inclusive by supporting the needs of this population.