Purpose: This study examined how labor–management relations between school districts and teacher associations seem to affect teacher contract provisions regarding the role of seniority in teacher assignment and how contract provisions and teacher assignment policies seem to affect beginning teachers’ perceptions about their work environments. Research Method/Approach: The study took place in five urban districts in a Midwestern state. In each district, we interviewed the human resource director and teacher association president, surveyed novice teachers in Grades 1 to 8, and examined the district’s collective bargaining agreement (CBA). We used district case reports to identify linkages between labor–management relations and contract provisions regarding teacher assignment. We drew on survey data to examine how these factors affected beginning teachers’ perceptions of their work environments. Findings: In four districts, the CBAs featured flexible language regarding the role of seniority in teacher transfer decisions. Principals had significant autonomy over teacher assignment, and assignment practices in these districts seemed fairly effective. In contrast, the CBA in the fifth district had rigid language pertaining to the role of seniority in transfer decisions and principals felt extremely constrained in making hiring decisions. Furthermore, analyses of the survey data suggested that beginning teachers in District D were less satisfied with their working conditions than novices in the other districts. Implications for Research and Practice: When districts and teacher associations engage in collaborative bargaining and adopt CBAs that provide principals with flexibility with regard to teacher assignment decisions, effective teacher assignment practices are likely to result.