This study is part of an ongoing design research to scaffold preservice teachers' higher-order reasoning while solving technology integration problems. Informed by previous iterations, we designed and examined progressively increasing scaffolds that integrated multiple scaffolding functions to facilitate three technology-based lesson design projects. The preservice teachers initially demonstrated superficial analysis, convergent ideation, and little evaluation when only limited procedural, conceptual, metacognitive, and strategic scaffolds were provided. Increased procedural and conceptual scaffolds in the second project improved the preservice teachers' analytic and generative reasoning skills, as they identified multiple challenges, technology tools, and lesson ideas to integrate technology. When the third project incorporated additional metacognitive and conceptual supports in structured procedural steps, the preservice teachers' analysis of teaching context, generation of lesson ideas, and evaluation of alternatives improved further. Based on these and previous findings, we proposed four principles of developing preservice teachers' higher-order reasoning skills during technology integration.