This study investigates changes in conjectures of four typical students when they are using different kinds of technologies, particularly in relation to their preferences for representations and the way they express their conjectures in understanding the concept and properties of iteration. The first stage of the research was conducted using pen and paper (PP) with graphical calculator (GC) in a classroom while the second stage used PP with graphical software (GS) in a laboratory. The findings suggest, with important caveats, that different technologies significantly influence the students' preferences for representations. Also, this study shows that students' conjectures can be an effective unit of analysis in researching students' understanding of iteration and preferences for representations