This study examined the associations between scale scores obtained from a teacher observation-based authentic assessment measure, the Teaching Strategies GOLD, and (a) teacher ratings of children’s social functioning and their learning behaviors and (b) child performance on individually administered direct assessments of academic skills. The sample was diverse and included 299 preschool children attending 51 different Head Start, public pre-k, and private school classrooms across 16 centers in the Northeast United States. Pearson correlation coefficients and a two level Hierarchical linear model (HLM) were used to assess the degree of association between GOLD scale scores and external measures. The correlations of the external measures with the GOLD domains were generally moderate and in expected, aligned areas. Findings suggest that the GOLD is a viable authentic assessment measure that taps preschool.