This study investigates how autonomy and self-confidence shape digital entrepreneurial intentions among youth in emerging Southeast Asian economies, where digital access is widespread but entrepreneurial uptake remains uneven. Grounded in the Theory of Planned Behavior, the research examines the psychological mechanisms driving this gap, focusing on autonomy as a predictor of confidence and confidence as a driver of entrepreneurial intent. Using survey data from 416 young adults in Malaysia and Singapore, Partial Least Squares Structural Equation Modeling (PLS-SEM) was employed to test direct and mediating effects. Results show that autonomy strongly predicts confidence (β = 0.761, p < 0.01), which in turn significantly influences digital entrepreneurial intention (β = 0.558, p < 0.01). Confidence partially mediates the autonomy–intention link (β = 0.425, p < 0.01), with the model explaining 69.6% of variance in intention (R2 = 0.696). These findings extend digital entrepreneurship theory by highlighting internal psychological resources as critical enablers of entrepreneurial action in digitally connected societies. The study offers actionable insights for educators, policymakers, and business ecosystem builders aiming to transform digital readiness into sustainable entrepreneurial ventures.