Help seeking is an important process in self-regulated learning (SRL). It may influence learning with intelligent tutoring systems (ITSs), because many ITSs provide help, often at the student’s request. The Help Tutor was a tutor agent that gave in-context, real-time feedback on students’ help-seeking behavior, as they were learning with an ITS. Key goals were to help students become better self-regulated learners and help them achieve better domain-level learning outcomes. In a classroom study, feedback on help seeking helped students to use on-demand help more deliberately, even after the feedback was no longer given, but not to achieve better learning outcomes. The work made a number of contributions, including the creation of a knowledge-engineered, rule-based, executable model of help seeking that can drive tutoring. We review these contributions from a contemporary perspective, with a theoretical analysis, a review of recent empirical literature on help seeking with ITSs, and methodological suggestions. Although we do not view on-demand, principle-based help during tutored problem solving as being as important as we once did, we still view it as helpful under certain circumstances, and recommend that it be included in ITSs. We view the goal of helping students become better self-regulated learners as one of the grand challenges in ITSs research today.