This qualitative study examined how and under what conditions pre-service social studies teachers reported transformations to their controversial issues pedagogy. This study began in 2011 and was situated in a pre-service social studies seminar at a graduate school of education in the United States. Data collection occurred in five different seminars and lasted three years. Afterwards, the authors met intermittently between 2014 and 2016 to establish findings. The study examined pre-service social studies teachers' responses to classes that utilized videotaped instruction of an experienced practitioner's lessons about controversial free speech and terrorism. The following question guided data collection: "How, and under what conditions, do pre-service social studies teachers report transformations to their controversial issues pedagogy when viewing videos of an experienced teacher?" The theoretical framework drew upon enlightened political engagement, and data was derived from the written reflections of pre-service social studies teachers in five different seminars. Findings emphasized that the pre-service social studies teachers were most likely to report pedagogical transformations when reflecting with a peer and when they were free to choose their analytical focus. Also, they were most likely to contextualize these pedagogical transformations within the observed teacher's classroom, a phenomenon we called 'transposing'. Implications of this study identify issues about how to teach for pedagogical transformations in controversial issues instruction.