This paper presents the results of a research study on preservice English teachers’ understandings of the interconnection of literacy and technology in relation to their teaching practices. The study was conducted in an English education program among preservice teachers enrolled in a year-long internship. The data analyzed consisted of interview and group discussion transcripts as well as semiotic artifacts (inquiry papers, written reflections, and short videos) produced by the seven participants. Particular attention was given to the ways school structures were affecting possibilities for productive transformations in the use of technology and the ways contradictory discourses were negotiated by the participants. Two contrasting approaches to the role of technology in the teaching of literacy were identified, which adopting Newman and Holzman’s (1993) terminology, were termed “tool-for-result” and “tool-and-result.” The paper concludes with an identification of the conditions afforded by the teacher education program and the school setting that facilitated the development of tool-and-result understandings among the preservice teachers.