This study aimed to investigate contract-based teachers’ experience from the perspective of teacher learning, based on the situated learning theory by Lave and Wenger. For this purpose, the study conducted in-depth interviews with 10 contract-based teachers working in secondary schools. As a result, in terms of the learning process, the study captured various aspects of participation according to the teachers’ disposition or the school context. While some participants showed a high level of teacher efficacy, others experienced isolation or exclusion from the teaching community, thus preferring to stay in peripheral positions. Also, due to the structural limitation of the contract, they had difficulty participating in practices that require long-term engagement. However, the study also found that contract-based teachers motivate new changes in the existing school community. Moreover, throughout the multifaceted process of learning, research participants were shaping their identity as contract-based teachers in their own ways. Based on these results, this study discussed the importance of legitimate peripheral participation for contract-based teachers and drew practical implications.