Self-regulated learning (SRL) skills are critical for students of all ages to maximize their learning. Two key processes of SRL are being aware of one's performance (self-evaluation) and believing in one's capabilities to produce given attainments (self-efficacy). To assess and improve these capabilities in young children (5–8), we use a literacy web application, where we introduced two randomly triggered prompts to evaluate perceived difficulty and desired difficulty. Comparing students' actual performance with their responses to self-regulatory prompts provides information about their ability to self-regulate their learning, in particular their self-evaluation and self-efficacy. The novelty of this work resides in studying the SRL of young children (5–8) in digital learning environments while learning another task (reading in our case), measuring and improving some SRL abilities themselves and not only measuring and improving academic results in other tasks, and the large number of students on which the studies were carried (over 400 000). Using 15 982 994 responses from 467 116 students, we first measured two types of SRL deficits, and then, we assessed how a scaffolding and remediation strategy can reduce these deficits. In Study 1, we compare a group receiving remediation feedback to a control group, whereas in Study 2, we determine the impact of age and level on the remediation efficiency. Our contribution is twofold: a method to address on the long term a deficit in self-evaluation or in self-efficacy in a digital learning environment, and a corroboration of the fact that students who are academically at risk lack self-efficacy and avoid tackling challenging exercises compared with their level. We, therefore, recommend that digital learning environments integrate an overlay of SRL, such as self-evaluation and self-efficacy remediation loops, especially for younger students and students who are struggling academically. We included notes for educational practitioners in this article for this purpose.