<p>Stress can adversely affect the emotional well-being of healthcare students, yet existing evidence is inconsistent. However, no meta-analysis has systematically examined these inconsistencies while recognizing emotional well-being as a multifaceted construct shaped by diverse stressors. Guided by the Transactional Model of Stress and Coping, Self-Determination Theory, and Resilience Theory, this meta-analysis contextualizes the stress–well-being relationship in healthcare students. The current study synthesized findings to clarify this relationship, treating emotional well-being as a multidimensional construct shaped by diverse stressors. A systematic search of PsycInfo, Scopus, PubMed, Web of Science, ScienceDirect, Oxford Academic, and gray literature sources identified 85 studies with 133 effect sizes (<i>N</i> = 32,029;&#xa0;<i>M</i>_age = 21.35&#xa0;years; 75.41% female). Using a three-level meta-analytic model, we found a significant negative association between stress and emotional well-being (<i>r</i> = –0.29, 95% CI: –0.36, –0.21,&#xa0;<i>p</i> &lt; .001). Heterogeneity was substantial between studies (<i>I</i>^<i>2</i>_{Level 3} = 89.54%), modest within studies (<i>I</i>^<i>2</i>_{Level 2} = 8.24%), and minimal at the sampling level (<i>I</i>^<i>2</i>_{Level 1} = 2.22%). The substantial heterogeneity underscores the variability of effects across contexts, highlighting the need for cautious interpretation and targeted interventions. Model comparison favored the three-level over the two-level approach (χ2 = 109.61,&#xa0;<i>p</i> &lt; .001). Moderator analyses revealed that type of emotional well-being, measurement tools, and demographic factors (country and developmental status) significantly influenced effect sizes. These findings provide robust evidence that higher stress levels are linked to lower emotional well-being, necessitating immediate targeted stress-reduction interventions, curriculum-integrated wellness programs, and comprehensive institutional policies for healthcare students.</p>