This paper examines students’ engagement in monitoring anomalous results across a 2-year longitudinal study with 9th and 10th graders (14–15 and 15–16 years of age). The context is a set of five inquiry-based laboratory tasks, requiring students to plan and carry out investigations. The study seeks to examine students’ interpretation of data, in particular anomalous results generated by them during the process of solving the tasks, and their ability to monitor them. Data collected include video and audio recordings as well as students’ written products. For the analysis, two rubrics were developed drawing on Chinn and Brewer (Cognition and Instruction, 19, 323–393, 2001) and Hmelo-Silver et al. (Science Education, 86, 219–243, 2002). The findings point to a pattern of progress in students’ responses across the 2 years: (a) responses revealing a low capacity of monitoring due to not recognizing the data as anomalous or recognizing it as anomalous but being unable to explain their causes are more frequent in the first tasks and (b) responses revealing an improved capacity of monitoring are more frequent in the last tasks. The factors influencing students’ regulation of their performances, as the requirement of planning, and specific scaffolding based on activity theory are discussed.