This study investigates the relationship between text-to-speech (TTS) usage and item-by-item performance in the 2017 eighth-grade National Assessment of Educational Progress (NAEP) math assessment, focusing on students with disabilities (SWDs), English language learners (ELLs), and their general education (GE) peers. Results indicate that all students use TTS more for longer and more difficult math items as well as for multiple-choice or short-response formats. Among SWDs and GE students, lower math proficiency and higher perceived time pressure are linked to higher TTS usage. Moreover, among GE students, factors such as male gender, minority status, lower math persistence, and higher math interest and effort during testing contribute to higher TTS usage. TTS usage is positively associated with item performance for SWDs and ELLs who received extended time accommodations but not for those who did not receive such accommodations or for general education students. The study suggests that the time constraints of speeded digital assessments may limit the potential benefits of TTS for SWDs and ELLs in math problem-solving.