Purpose: This study examines policies set in the collective bargaining agreements (CBAs) negotiated between teachers' unions and school boards and explores what kinds of districts have contract provisions that restrict district administrators, enhance administrative flexibility, and/or improve teachers' professional work lives and that have contracts that are more restrictive overall. Method: The author analyzes a sample of 465 California CBAs and uses linear probability models to highlight the relationships between a set of 95 representative provisions and characteristics of districts that may make them "hard to staff." A measure of overall contract restrictiveness is generated and used to assess the relationships between these district characteristics and contract strength. Findings: Some CBA provisions restrict district administrators, whereas others may provide administrators with greater flexibilities. In addition, many provisions serve to enhance teachers' working conditions. Many of the most restrictive clauses are more frequently found in the contracts of urban districts and districts with higher proportions of minority and poor students. However, many of these same districts have contracts that include important flexibilities and provisions that may enhance teachers' working conditions. Large and urban districts have more restrictive contracts overall, although districts with high proportions of poor and minority students do not. Implications: As policymakers consider renegotiating provisions within CBAs and diminishing the strength of CBAs themselves, it will be important to consider the specific regulations within CBAs and whether they truly constrain administrators or serve some other purpose and whether specific high-need districts are more or less harmed by the contents of CBAs. (Contains 3 tables and 9 notes.)