Although internalizing problems are the most common forms of psychological distress among adolescents and young adults, they have precursors in multiple risk domains established during childhood. This study examined cascading risk pathways leading to depression and anxiety symptoms in emerging adulthood by integrating broad contextual (i.e., multiple contextual risks), parental (i.e., negative parenting), and child (i.e., internalizing behaviors) characteristics in early and middle childhood. We also compared common and differential pathways to depression and anxiety symptoms depending on the conceptualization of symptom outcomes (traditional symptom dimension vs. bifactor dimensional model). Participants were 235 children (109 girls) and their families. Data were collected at 3, 6, 10, and 19 years of child age, using multiple informants and contexts. Results from a symptom dimension approach indicated mediation pathways from early childhood risk factors to depression and anxiety symptoms in emerging adulthood, suggesting common and distinct risk processes between the two disorders. Results from a bifactor modeling approach indicated several indirect pathways leading to a general internalizing latent factor, but not to symptom-specific (i.e., depression, anxiety) latent factors. Our findings highlighted comparative analytic approaches to examining transactional processes associated with later internalizing symptoms and shed light on issues of early identification and prevention.