Reflection represents an important form of human thought; from ancient to modern times, the human capacity for reflective thinking has held the imagination of various philosophers and educational theorists. Despite this interest, researchers define reflection in different ways. One of the purposes of this article is to explore the activity of reflection by examining characteristics and contextual factors associated with it. For this purpose, various philosophical and theoretical sources are considered including Socrates, Rousseau, and Bruner, among others. Following this, empirical research is examined to determine whether elements associated with reflection are consistently integrated within regular classroom instruction. Next, practical and theoretical obstacles to reflection are proposed. One of these obstacles is an over-emphasis on the technical interest, a concept described by Jürgen Habermas. Last, some implications are suggested with regard to the use of reflection as a construct for infusing new points of discussion in teacher education and practice.