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The present study explored the utility of a widely used performance-based assessment of children’s readiness skills as a kindergarten entry assessment. In a sample of 520 kindergarten students across 52 classrooms, we compared students’ school readiness skills as assessed by teachers using Teaching Strategies GOLD (TS GOLD) to direct assessments administered by independent data collectors. We found evidence of the concurrent validity of TS GOLD. However, the measure demonstrated weaknesses in its ability to differentiate readiness skills. Specifically, the highly correlated latent constructs and intraclass correlations associated with TS GOLD indicated that teachers were less likely to differentiate readiness skills among children within the same classroom relative to direct assessments. The findings are discussed in terms of assessing children’s school readiness at scale. As the number of programs, districts, and states that require school readiness assessments increases, so does the need to better understand the information that can be inferred from particular methods of assessment.