Drawn from an investigation of the emergent technological practices of post-secondary students with mathematics learning disabilities, this case study employs an enactivist framework in considering the bootstrapping processes our participants report engaging in when using personal electronic devices for academic support. Video-recorded, semi-structured interviews were conducted with nine post-secondary participants with mathematics learning disabilities in two western Canadian urban centres. Findings suggest that participants used technology to control and improve sensory input in order to better access mathematics course content and monitor the accuracy of their work, engage with alternate presentations of mathematical concepts to enhance their level of understanding, reduce workload, and improve organization. We discuss how their strategies in using technology relate to Bereiter's categorization of bootstrapping resources (1985), including imitation, chance by selection, learning support systems, and piggybacking. Grounded in a "learner's perspective," this case study identifies technological adaptations and strategies that may be helpful to others with mathematics learning disabilities.