This study examines the relationships between three accommodation strategies--Extended Time (ET) only, breaks only, and breaks bundled with ET--and academic performance, test-taking behavior, and attitudes among eighth-grade students with disabilities who participated in the 2017 National Assessment of Educational Progress (NAEP) mathematics assessment. Utilizing propensity score analysis to mitigate selection bias, the study finds that students receiving only breaks tend to exhibit lower performance and engagement compared to those receiving ET alone or those receiving breaks bundled with ET. In addition, results suggest that bundling breaks with ET is associated with lower performance compared to ET alone. These findings highlight the complexities of interactions between accommodations and support the need for reevaluating current accommodation policies to enhance their effectiveness for students with disabilities. [This article was published in "Remedial and Special Education."]