This study investigates the hypothesis that students' learning and problem-solving performance in ill-structured domains can be improved, if elaborative question prompts are used to activate students' context-generating cognitive processes, during case study. Two groups of students used a web-based learning environment to criss-cross and study case-based material in the software project management domain. The experimental group was additionally prompted to consistently answer a set of questions based on a model of context-generating processes, meant to engage students in deeper processing of information presented in cases. Students were also classified as having either "complex" or "simple" EB profile (based on their epistemological beliefs record), thereby establishing a 2x2 factorial design. Results indicated that scaffolding treatment had a significant main effect on students' performance, with the experimental group performing better in both domain knowledge acquisition and knowledge transfer post-test items. There is also tentative indication that EB profile and scaffolding treatment interact, with complex-EB learners benefiting most from the scaffolded condition. Overall, the study provides evidence that it is possible to improve individual learning in a technology environment for case-based learning, by implementing appropriate questioning strategies that trigger students to activate their context-generating cognitive processes, while studying the contextually rich material of cases.