This Research Work in Progress Paper presents our ongoing work to encourage student to reflect while participating in a distributed self-assessment process. We shed light on the case of low reflect participation and the change in process we made that led to a significant increase in both the quantity and quality of students reflects. To evaluate the effect of the intervention, we conducted two classroom study for an introductory Java course with over 500 students. From the latest enhancements in the current study, we observed that the overall reflecting engagement from the students has significantly increased compared to our initial work. To evaluate the reflects quality, we deployed an automated measure that classifies the constructiveness of the comment based on its relevant and subjectivity to the domain. This work describes the details of the interventions along with the resulted observations. The main objective was to encourage learners to provide thoughtful reflects which we were able to increase along with the positive effect on their performance.