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Previous investigations mostly relied on the two-factor model of grit (with perseverance of effort and consistency of interests as major dimensions) which received a number criticisms in the extant literature. Recent studies have provided promising lines of evidence regarding the triarchic model of grit (TMG) which posits three dimensions of grit in a collectivist setting: perseverance of effort, consistency of interests, and adaptability to situations. However, little is known about how this model of grit may be linked to various indicators of positive educational and psychological functioning. The present research filled this gap through examining the association of the TMG with academic (Study 1) and well-being outcomes (Study 2) among Filipino high school students. Results demonstrated that grit positively predicted academic agentic, behavioral, cognitive, and emotional engagement. Findings of multiple mediation analyses showed that grit had indirect effects on academic engagement via the intermediate variable autonomous motivation even after controlling for age, gender, and conscientiousness. Study 2 showed grit positively predicted life satisfaction, positive affect, and interdependent happiness even after controlling for demographic covariates and neuroticism. Grit negatively predicted psychological distress. Theoretical and practical implications are discussed.