Teacher attrition, particularly of beginning teachers, is concerning. Extensive research has been conducted on teacher attrition and teacher characteristics; however, less research exists on teacher retention and related teacher belief systems. This study examined the beliefs of a particular subset of teachers—teachers who have stayed in the profession in their first 3-5 years (N = 67). It explored if and how initial and current beliefs about students buffer the challenges teachers face in their entry years in the profession, if these beliefs change across time, and if these beliefs vary across grade level and school-level socioeconomic setting (SES). This study also examined a subset of teachers (n = 21) to explore how preservice teacher and classroom observation data can inform teachers’ beliefs about student learning in their first years of teaching. Results indicated that teachers’ beliefs about students become more integrated across time and demonstrate growth in expertise in teachers’ beliefs about students. Also, teachers held more positive perceptions of students over time in addition to a greater emphasis on the importance of preparation, completion, trying another way when you struggle, finishing strong, and having a plan when you are done. Grade level differences in beliefs existed in the first year, but disappeared across time. Further, no significant differences in beliefs about students across school-level SES were present as teachers entered the classroom and did not change as they adapted to these settings. The positive and more coherent beliefs that teachers held in their third, fourth, and fifth year of teaching (as compared to their first) suggest that these beliefs help them cope in their first five years in the profession.