Work-integrated learning (WIL) students are exposed to a range of stressors that can impact wellbeing. However, there is a paucity of research exploring stress prior to the work experience, such as in the job search and application process. To address this issue, semi-structured interviews were conducted with 25 undergraduate first-year cooperative education students. Students reported that job applications and interviews were particularly stressful events, with job applications having the greatest impact on wellbeing, influencing physical, emotional, and social health. These events were stressful because they involved competition, tight deadlines, uncertainty, and the juggling of academic and WIL commitments. Students were most likely to employ approach strategies to cope with the stress, seeking out support and resources. Our findings highlight the wellbeing impacts that stressful events in the job search and application process can have on students. Limitations of the study and recommendations for mitigating the negative impacts of this process are discussed, including the importance of support networks and the timing of interventions.