Background/Objectives According to existing evidence, parental educational practices and social anxiety are to some degree connected. However, the possibility that this relationship is an indirect one and is mediated by individual factors such as self-esteem or emotional regulation has not yet been explored. The aim of this study was therefore to explore the relationship between maternal and paternal educational practices and social anxiety, and test both the direct and the indirect pathways. Method: The representative sample consisted of 2,060 Andalusian students (47.7% girls, M age = 14.34) who filled in various self-reports. Results: The structural equation models confirmed that a direct relationship, with a low effect size, exists between parental educational practices and social anxiety and that there is also an indirect relationship, mediated by negative self-esteem and emotional suppression (the emotional regulation strategy), which accounted here for 49.1% of the variance in social anxiety. Conclusions: Parental education practices seem to act as a family asset which either promotes or hinders the development of basic attitudes and competencies such as self-esteem or emotional regulation and, by doing this, either encourages or prevents the emergence of problems such as social anxiety.