This study explores how preservice teachers (PSTs) transfer the intended specialized content knowledge (SCK) to elementary classrooms. Focusing on the case of the associative property of multiplication, we compared three PSTs' SCK during enacted lessons in fourth grade classrooms with their own learning in professional development (PD) settings. Findings revealed the PSTs' successes and challenges in unpacking an example task, especially in areas of making connections between concrete and abstract representations and asking deep questions that target quantitative interactions. Factors that may have supported or hindered PSTs' SCK transfer include the complex nature of teacher knowledge, the PD effort and the outside factors such as the support from textbooks and cooperating teachers. Implications for teacher education and directions for future research are discussed.