The present study set out to delineate to what extentfive intermediate learners engaged in structuring and problematizing scaffolding in two writing tasks. The study aimed at illuminating how the participants engaged with structuring and problematizing scaffolds cognitively, behaviorally, and affectively. Learners’ written essays, think-aloud protocols, and interviews shaped the data sources which were analyzed both quantitatively and qualitatively. Modifications made in the final drafts were quantitatively analyzed to provide insight into the behavioral engagement of participants with scaffolds. The profundity of cognitive engagement was gauged by the interview questions designed to elicit the depth of processing and illuminate whether participants had merely noticed the existence of a problem or they had understood what was required to be done. Researcher also compared the use of cognitive and metacognitive operations after learners were presented with structuring and problematizing scaffolds through the analysis of think-aloud protocols generated in final drafts each session. Finally, attitudinal and affective engagement was gauged qualitatively through interviews. The results indicated that structuring scaffolds engaged learners more behaviorally, cognitively, and affectively compared to problematizing scaffolds. Implications for instructors and material developers are discussed.