Teacher education programs attempt to prepare preservice teachers for the various challenges faced in the classroom. One particular challenge new teachers face is how to handle unsuccessful practices. This paper argues that confronting ineffective practices require that teachers respond to complex and dynamic challenges, making change difficult when solutions are not readily available. Presenting data from case-study research, the paper uses an identity framework and positioning theory to explore how two novice teachers navigate moments of unsuccessful practice. Findings suggest that when teachers confronted ineffective practices they repositioned their teacher identities in ways that depended on the ideologies of their school. The paper concludes with implications about the importance of extending typical reflective practices of teacher education with video analysis that challenges students to examine how they enact teacher identities over time within the figured world of their school.