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This study introduces a Generational Analysis Framework to examine how parent (P), grandparent (GP), and great-grandparent (GGP) comments influence toxicity transmission in hierarchical online conversations. Rather than assigning a single toxicity label to an entire thread, the framework analytically characterizes whether the terminal comment of a conversation tree is toxic or non-toxic, using generational ancestor features as analytical instruments. We analyze 1.2 million Reddit posts from r/NoNewNormal (June 2020–August 2021), structured into 156 847 conversation trees, from which 23 000 trees with at least four hierarchical levels are identified for P-GP-GGP analysis. Toxicity is detected using Detoxify (RoBERTa-based), and nine machine learning algorithms are evaluated as analytical instruments. Statistical validation includes 95% power analysis, bias assessment via chi-square test (
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