Experiences of failure can provide valuable opportunities to learn, however, the typical classroom does not tend to function from an orientation of learning from failure. Rather, educators aim to teach accurate information as efficiently as possible, with the main goal for students to be able to produce correct knowledge when called for, in the classroom and beyond. Alternatively, teaching for failure requires instructional designs that function out of a different paradigm altogether. Failures can occur during activities like problem solving, problem posing, idea generation, comparing/contrasting cases, or inventing formalisms or pattern-based rules. We present findings from a study done in fourth-grade classes on environmental sustainability that used a design allowing for failures to occur during collaboration. These center on dialogs that included "micro-failures," where we could address how students deal with failure during the process of learning. Our design drew from "productive failure," where students are given opportunities to fail at producing canonical concepts before receiving explicit instruction, and unscripted collaborative learning, where students engage in collaboration without being directed in specific dialogic moves. By focusing on failures during an unscripted collaborative process, our work achieved two goals: (1) We singled out occurrences of failure by analyzing students' dialogs when they encountered impasses and identified several behaviors that differentially related to learning; (2) We explored how the form of task design influences the collaborative learning process around failure occurrences, showing the potential benefits of more structured tasks.