This study investigates the effectiveness of two variants of a prompting strategy that guides students to focus on important issues when learning in an ill-structured domain. Students in three groups studied individually Software Project Management (SPM) cases for a week, using a web-based learning environment designed especially for this purpose. The first group (control) studied the cases without any prompting. The second group ("writing mode") studied the same cases, while prompted to provide written answers to a set of knowledge integration prompts meant to engage students in deeper processing of the material. The third group ("thinking mode") studied the cases, while prompted only to think of possible answers to the same question prompts. Results indicated that students in the writing condition group outperformed the others in both domain knowledge acquisition and knowledge transfer post-test items. Several students in the thinking condition group skipped the question prompts, while those that reported having reflected on the material were unable to achieve high performance comparable to the writing condition group. Overall, the study provides evidence that the implementation of prompting techniques in technology-enhanced learning environments may lead to improved outcomes, when combined with the requirement that students provide their answers in writing.