Background: Independent Student Expeditions (ISE) are small-group learning activities regularly incorporated into outdoor experiential education (OEE) programming. Research suggests they yield valuable outcomes for participants; however, little is known about how groups that operate independently of their instructors regulate themselves to navigate the challenges they face. Purpose: To examine how OEE students regulate collaborative learning activities when instructors are absent or their role is less prominent, so we can offer insights into effectively utilizing ISE and other autonomous experiences as pedagogical tools. Method: Data were collected from NOLS semester students using a paper-and-pencil survey. To complement the survey data, a subset of participants completed follow-up interviews. Findings: ISE groups employed a variety of group and self-regulatory strategies to manage the challenges encountered during the ISE, allowing them to approach this course component as an opportunity for learning. Implications: Our data revealed three primary ways that instructors can help prepare groups for independent, collaborative learning: (1) help small collaborative learning groups learn how to regulate; (2) help individuals learn how to self-regulate; and (3) consider important structural components, like group member composition, before providing participants with independent learning experiences.