Heuristics are deeply-held, tacit knowledge structures connected to our feelings. A heuristic study explores a phenomenon crucial to the researcher's self-discovery (Moustakas, 1990). Like me, many undergraduate composition instructors feel both fear and hope at the crossroads of composition and technology. Technology and composition shape one another in a complex mutual relationship with many other factors (Lincoln and Guba, 1985). Metaphorically, the intersection of technology and composition compares to a roundabout with many streams of traffic merging and diverging rather than creating a simple traffic intersection. One crucial factor in the stream is the heuristic assumptions of the instructors in the trenches. In this study, I explore our feelings about how technology impacts (1) composition or what we teach, (2) instruction or how we teach, (3) our professional self-definition. I triangulated data from a variety of sources. I began with my own self-dialog. Then I emailed a survey to faculty members in fourteen English departments. To create a purposeful sample for maximum variation, I chose six participants: three opponents and three proponents. I divided the participants into (1) digital pioneers, (2) digital immigrants, and (3) digital natives. I interviewed three participants directly and three digitally. Finally, I created composite and individual portraits. The composite portrait of technology proponents showed a tendency to (1) differentiate instruction, (2) value new communication mediums, (3) focus on learner-centered education, (4) feel pedagogies of the past inadequate, (5) risk failure. The composite portrait of technology opponents showed a tendency to (1) focus on critical thinking, (2) view technology as a tool, (3) fear technology glitches, (4) resent pressure to use technology. For the individual portraits, I focused on digital immigrants, including my own. Colby (2006) suggests understanding digital immigrants contributes to understanding the phenomenon. By comparing portraits, I uncovered five transformed heuristic assumptions: (1) my linking composition and technology through andragogy, (2) fear that technology may negatively impact my career, (3) a link between technology-use and my professional self-definition, (4) value in finding my voice, (5) value in being a digital immigrant. At this crossroads, we as composition teachers should critically reflect on our heuristic assumptions about composition and technology. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]