In the following self-study, I consider how my involvement in a teacher preparation program that features looking across multiple contexts of second language teaching influenced my supervisory practice with a particular student teacher during her secondary foreign language student teaching placement. I conduct this inquiry by identifying and reflecting upon instances in which I made connections across contexts during postobservation conferences with this student teacher as well as instances in which I neglected to make connections. To conclude, I discuss the potential of preparing and professionally developing teachers from different second language contexts together.