Through access to assistive technology, adult students with learning disabilities can improve their literacy skills and goal attainment as a supplement to regular adult basic education classes. This article describes a project that investigated whether increased engagement with text-to-speech and speech-recognition software could improve participants' foundational literacy skills. Data were gathered through careful observations as well as reflective dialogue with the learners. Three layers are explored: (1) The underlying framework of dialogic research; (2) Thematic analysis of students' interactions with the equipment; and (3) Thematic analysis of the role of the coach. Through a series of snapshots of students' approaches to literacy learning with assistive technology and a cross-case analysis, possibilities and complexities are revealed in the intersection of literacy and technology. (Contains 1 figure.)