In this article, we explore challenges encountered by K-12 educators in establishing classroom cultures that support creative learning activities with the Scratch programming language. Providing opportunities for students to understand and to build capacities for creative work was described by many of the teachers that we interviewed as a central aspiration of learning and education. But creative learning is an iterative process that necessarily involves moments of getting stuck, not knowing, being wrong, and failing--moments that conflict with how learning is enacted in many school settings. 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.