This qualitative study illuminates the challenge of preparing teacher candidates to engage critically about social justice issues in their planning and instruction in a yearlong teacher education credential program in a northern California university. Using co-narrative to describe the study in tandem with thematic analyses of candidates' artifacts from a critical pedagogy framework (Duncan-Andrade & Morrell, 2008; Freire, 1970) and a critical literacy framework (Cadiero-Kaplan, 2004; Shor, 2009), we found that (1) instructional themes and topics in candidates' lesson plans do not often broach the realities and experiences of the linguistically and culturally diverse students in their classrooms; (2) themes and topics of lessons are indicative of candidates' tendency to play it "safe" with regard to critical theory teaching while adhering to high-stakes testing mandates and expectations within site placements; and (3) student teachers need additional modeling and scaffolding within their teacher preparation program along with support from their cooperating teachers within their site placements to actualize critical pedagogy and multicultural education tenets. The paradox: A more prescriptive and conscious approach must be used with candidates to (1) analyze "diversity" through the real circumstances of their students and (2) reflect critically on their positionality and paradigm, the "act of teaching," and what that entails within a U.S. high-stakes testing climate. (Contains 1 table and 10 notes.)