Engaging students in a challenging (cognitively demanding) task and launching a mathematics lesson with a task before instruction are two characteristics of a reform-oriented approach to mathematics instruction often considered together. The authors systematically contrasted teaching with challenging tasks using a task-first lesson structure with that of a discussion-first lesson structure to three composite classes of first- and second-grade students (n = 73). Subsequent assessments of mathematical performance revealed that the discussion-first lesson structure was somewhat more efficacious in improving fluency performance but both structures similarly improved problem-solving performance. The findings suggest there is more than one way of incorporating challenging tasks into mathematics lessons to produce sizeable learning gains.