Objective <p>This study aimed to evaluate the factors influencing parental treatment preferences during the management of their children’s first permanent molars indicated for endodontic retreatment.</p> Methods <p>A cross-sectional study was conducted involving a sample of 73 adolescents aged from 10 to 17 years and their parents. Sociodemographic data, treatment preferences, and underlying reasons were recorded. Clinical and radiographic examinations were performed for the evaluated teeth. DMFT, DMFS, and PUFA index scores were determined through the intraoral assessments. Parental dental anxiety and perceived child anxiety were quantified using the Modified Dental Anxiety Scale (MDAS). Data were statistically analyzed.</p> Results <p>Parental treatment preferences were predominantly in favor of retreatment (67.1%), followed by the “Wait-and-See” approach (23.3%), while extraction was least preferred. No significant associations were found between parental preferences and sociodemographic variables, patient gender, clinical/radiographic findings, or treatment history (<i>p</i> &gt; 0.05). However, the child’s age was significantly associated with parental preference (<i>p</i> = 0.038), with increasing age associated with a higher likelihood of choosing extraction. In multivariate analysis, the child’s age (OR = 1.89, <i>p</i> = 0.038) and a short root canal filling level (OR = 32.40, <i>p</i> = 0.037) were identified as significant independent predictors of preferring extraction over a “Wait-and-See” approach.</p> Conclusion <p>Parental knowledge and previous dental experiences may influence on the treatment decision-making process. Enhancing parental awareness may encourage more conservative treatment choices in adolescents.</p>