ABSTRACT This study addressed the challenges faced by pre- and novice in-service teachers coping with metacognition in the context of teaching higher order thinking (HOT). Our purpose was to reveal and characterize the participants’ metacognitive knowledge and pertinent pedagogical knowledge. We followed pre- and novice in-service teachers who participated in a preparation course for teaching HOT and metacognition, examining both their planning for and actual application of metacognitive instruction in the classroom. We used mainly qualitative research methods, including an open-ended questionnaire, and a thematic analysis of lesson plans, classroom observations, and interviews. we found that most of the participants were able to apply the knowledge studied in the course to develop new learning activities aimed at promoting students’ metacognitive thinking. Novice teachers were also able to apply metacognitive instruction in their classrooms. Participants tended to integrate metacognitive instruction in familiar, traditional teaching patterns rather than in more progressive ones and exhibited several additional challenges that are specific to metacognitive instruction. The implications for preparing and supporting prospective and beginning teachers for metacognitive instruction are discussed.