This study examined factors at the school, district, and provincial level that influenced school administrators’ responses to large-scale assessment. To understand administrators’ perspectives, 5 secondary and 4 elementary administrators from a suburban school district in southern Ontario, Canada were interviewed. Key factors noted by administrators included school improvement planning (elementary versus secondary), departmental structures and teacher resistance within schools, lack of professional development opportunities, inadequate resources and direction from districts, ministry initiative overload, lack of an easily identifiable provincial assessment and evaluation policy document, and pressure to reach provincial achievement targets. The findings underscore the need for greater initial and ongoing professional development for school administrators as well as more thoughtful support from district leaders and provincial policy-makers.