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This study investigates whether and when parental engagement in adolescents’ home-based learning affects students’ academic failure experience in daily learning. In a longitudinal four-wave time-sequential study with 2377 Austrian students at the age of 11 to 15 from grade 5 to 8, self-reported academic failure experience was measured at each time point. Generally, higher levels of parental engagement were associated with a decrease in the level of academic failure experiences. The largest effect of perceived parental engagement is found in early adolescence between grade 6 and 7. The results are discussed against the backdrop of Eccles’ Stage-environment fit theory, in terms of puberty onset as a vulnerable period when parental support is needed most.