This article presents an iterative study to bring out “practical and pedagogical issues of translanguaging in the classroom” (p. 491). The study involved interviews with three groups of stakeholders from four multilingual high schools: language education researchers, teachers, and multilingual learners. The authors interviewed a range of stakeholders to capture translanguaging “pedagogical challenges (real or perceived)” and their “views on those challenges” (p. 508). As a result, a total of seven pedagogical challenges emerged from the study analysis: 1) Side effects, 2) Goal formulation, 3) Learning the language of schooling, 4) English and other semiotic resources, 5) Affective functions, 6) Effort, and 7) Confusion. The results elaborate on each pedagogical challenge, highlighting that addressing these issues can provide guidance in the implementation of translanguaging pedagogies and practices in multilingual schools.