Self-regulated strategies development framework applied for writing has produced some of the most powerful results in writing for all age level students. The success has been attributed to the multiple theories integrated to design the intervention and careful focus on different types of support for instruction and assessment related to modeling, motivation, self-regulation, and practice related to students’ declarative, procedural, and conditional knowledge about writing and strategy use. Many SRSD writing interventions were delivered by teachers or researchers with careful consideration for all student factors. We Write was the first web-based SRSD writing software that was designed to work in concert with teacher-led delivery of intervention. Essential to the entire framework is the reliance on strong and high quality assessments to inform instructional moves to support mastery learning. Developing technologies for learning is much more complicated than most people acknowledge (Cheung & Slavin, 2012). In the We Write system; our design choices were customized to the multi-faceted nature of the SRSD instruction and assessment requiring different types of interactions depending on the progression of the learning process. Consequently, each computer activity was guided by the nuanced needs of the SRSD framework to instruct, model, assess, and scaffold different activities designed to promote students’ declarative, procedural, and conditional knowledge about writing and strategy use. In this Chapter, we present samples of the many different types of We Write activities with the rationale for their choices, varying scoring approaches, and how upper elementary grade students performed on each task.