The paper is a reflection on the author’s work with students enrolled in undergraduate and graduate elementary mathematics content and methods courses. Two specific pedagogical issues make up the focus of the paper. The first issue deals with demonstrating to future teachers the diversity of mathematical ideas behind a contextual question asked by a second-grade pupil allowing for multiple solution strategies to be used in addressing the question. The second issue deals with the use of Wolfram Alpha in aiding different mathematical features of this demonstration. The paper is congruous with mathematics teaching standards used across six continents and illustrated by reflective comments of the author’s students regarding their mathematics teacher education experiences. Teaching ideas shared in the paper may be of interest to instructors who want to explore elementary mathematics in depth with teacher candidates.