The focus of this study is to determine how closely self-report perceptions of technology integration skills align with the observations of an external evaluator. Participants were elementary and secondary teachers in a north Texas school district. The district is in the process of implementing a one-to-one initiative using a major vendor’s tablet devices. The study utilized both quantitative survey methodology, and a qualitative observational tool to record learning activities in the K-12 classroom. For the quantitative phase, three validated single-item self-report instruments were administered to the teachers via an online survey; the instruments utilized were the Concerns-Based Adoption Model—Levels of Use (CBAM-LoU); Stages of Adoption of Technology; and the Apple Classroom of Tomorrow (ACOT). In the qualitative portion of the study, classroom teachers involved in the one-to-one innovation were observed and rated by the Technology Integration Matrix, an instrument specifically designed to observe technology integration skills and practices in K-12 instructional settings. Kendall’s tau correlations between the various self-report instruments and the external observer rating are: CBAM, r = .51 (p is not significant); Stages, r = .58 (p < .05); ACOT, r = .82 (p < .01). Additionally, regression models were run using all three self-reports as predictors of the observation score, and using only the ACOT as a predictor. The regression model for the three-predictor model is TIM = .68; Stages - .82; CBAM + 1.61; ACOT - 1.23 (R2 = .94, p < .05), while the model for the ACOT-only predictor is TIM = 1.1; ACOT - 1.1 (R2 = .80, p < .01). These results demonstrate a strong correlation between the ratings reported by the teachers and the ratings given by the external observer, indicating that these self-report measures show a strong propensity for indicating actual technology skills.