The lack of contextual assessment instruments that promote higher-order thinking skills (HOTS) contributes to Indonesian students’ low performance in international assessments such as the Programme for International Student Assessment (PISA). This study aims to design contextualized PISA-like mathematics problems on number content for junior high school students to enhance their HOTS. This research employed a design research approach of the development study type, consisting of preliminary and prototyping stages. Six items were developed to represent the six cognitive levels of PISA. The instruments were evaluated through expert review, one-to-one, and small group testing, and analyzed using qualitative and quantitative methods. The results indicate that the developed instrument is valid in terms of content, construct, and language, with a very high reliability coefficient (0.923). The items demonstrate appropriate levels of difficulty and good discriminating power, and are effective in supporting students’ mathematical reasoning. The use of contextualized everyday situations helps students connect abstract numerical concepts with real-life experiences. However, students still require scaffolding when solving higher-level cognitive tasks. These findings suggest that the developed PISA-like problems are feasible as an alternative assessment tool to enhance students’ higher-order thinking skills in mathematics learning.
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