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This study examined dynamic changes in parental autonomy support and controlling behavior during a 15-minute parent–child math homework interaction. Forty-four parent–child dyads (2nd grade; 55% girls) from the United States were observed and coded using a behavioral coding scheme for autonomy support and control. Results showed that, on average, parents’ autonomy support declined while their control increased over the course of the interaction. Importantly, parents of children with higher math anxiety showed a steeper decline in their autonomy support (vs. control) over time compared to those of children with lower anxiety. These findings underscore the difficulty of maintaining constructive involvement during math homework help and highlight the importance of equipping parents with strategies to remain supportive in challenging learning contexts.