This study examined the midterm exams of six high school math teachers and sought to (a) determine if teachers could accurately identify which level of Norman Webb’s Depth of Knowledge (DOK) model their test items aligned to, and (b) compare the actual percentage of test items at each DOK level to the targeted percentage based off Webb’s research. The study revealed that teachers were not accurate with their alignment of test items with Webb’s DOK model. They also came up short in comparison to the targeted percentages of test items at each level. Comprehensively, they were asking more questions at Level 1 and 2 instead of at Level 3 or 4. Recommendations are provided on how teachers can write questions at the targeted level for their course. Advancing high school students’ depth of knowledge (DOK) in mathematics can be challenging, so it is important for assessments to meet the appropriate levels of DOK. Finally, assessing the DOK levels of created test items is a task that can be difficult for most high school teachers. These challenges were the backdrop of this study.

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