This study compares the effects of forum discussion with metacognitive guidance versus forum discussion without metacognitive guidance (Forum) on solving real life mathematical tasks and self-regulated learning. Participants were 43 Grade 7 students (boys and girls) who practiced online problem-solving in two classes. The metacognitive guidance was based on the IMPROVE metacognitive questioning suggested by Mevarech and Kramarski. The method utilized a series of four self-addressed metacognitive questions: comprehension questions; connection questions; strategic questions; reflection questions. It was found that students who were exposed to forum discussion with metacognitive guidance (Forum+Meta) outperformed students that were not exposed to metacognitive guidance (Forum discussion) on real life mathematical tasks and self-regulated learning. It was found that the Forum+Meta students were more positive than the Forum students about their interest in online problem-solving, mathematical engagement and online communication.