<p>Enhancing students’ ability to create mathematical problems significantly contributes to their development of critical thinking, creativity, and problem-solving skills in mathematics learning. Therefore, this study aimed to investigate the effect of context-based problem-posing and solving instructional approaches on the fifth-grade students’ problem-posing skills in learning data handling. The study also sought to investigate how students thought of developing problem-posing skills. To this end, the study employed a concurrent embedded quasi-experimental non-equivalent pre-test-post-test control group mixed-method design. A total of 138 fifth-grade students participated in the study. Data were collected using problem-posing skills tests, lesson observations, and semi-structured interviews. Quantitative data were analyzed using descriptive statistics, paired sample t-test, and ANCOVA. Qualitative data were analyzed thematically. The study revealed that context-based problem-posing and solving instructional approaches significantly improve students’ problem-posing skills. When compared to the comparison group, a medium level of effect size has been observed on the post-total data handling and post-context-type data handling problem-posing skills. Integrating context-based problem-posing and solving in learning data handling significantly enhances students’ problem-posing skills and fosters a sophisticated developmental progression from surface-level cultural substitutions to deep structural modelling involving data visualization. Developing context-based problem-posing and solving instructional materials, along with a prolonged duration of intervention, is recommended for future studies.</p>