The purpose of this pilot case study was to answer the following research questions: How do previous experiences affect students' attitudes toward online teamwork? When do students' attitudes toward online teamwork first develop and why? Using a social constructivist framework, a qualitative case study design was utilized to conduct an online open-ended survey and online focus group in one online Organizational Leadership 300-level course. Findings revealed that students' attitudes toward online teamwork are in part predicated upon previous online team experiences. Students identified a number of challenges with online teamwork, many of which related to personality issues, slackers or members who do not contribute his or her share of the work, and poor communication. Generally, students' attitudes and perceptions toward online teamwork began in college after their first online team experience. In order for online teamwork to be effective, instructors may consider designing team projects that include methods to ensure both team and individual accountability, promote team cohesiveness, and foster frequent communication among team members.