In this article, the authors explore challenges encountered by K-12 educators in establishing classroom cultures that support creative learning activities with the Scratch programming language. The analysis is organized into three thematic clusters that elaborate this conflict: teacher vs. self, teacher vs. student, and teacher vs. culture. Teacher vs. self explores the role of teacher identity and psychology in supporting creative activities in the classroom. Teacher vs. student discusses unanticipated resistance from young learners encountering creative activities in school settings. Teacher vs. culture describes how expectations from beyond the classroom setting can constrain creative activities within the classroom, including the role of parents, administrators, and policy.