College students face many challenges, including life transitions and academic and social stressors, which can impact their overall well-being. Digital mental health (DMH) tools can assist in managing these stressors through self-tracking approaches that collect personal data and provide insights into health status. However, to effectively help individuals to manage stress, it is crucial to offer direct guidance on actionable steps for change. To explore this domain, we developed a system with an automated recommendation feature as a technology probe to investigate how personalized health recommendations can support college students in stress management. We conducted a user study with 20 college students to learn from their experiences. Our analysis reveals participants’ insights on the effectiveness of recommendations in motivating self-care and the benefits of using personalized recommendations to guide individual actions. Based on our findings, we discuss strategies and design implications to further support college students in managing stress.