The study examined the relationship between parents’ characteristics (occupation, educational attainment, degree of religiosity), family background (family structure and size) and cognitive self-reliance of senior secondary school students in Ekiti State, Nigeria. The sample for the study comprised 423 students and their parents (816) using a simple random sampling technique, while two schools from each Local Government Area were selected purposively because only co-educational public secondary schools with no boarding facilities were used for the study. The students and the parents responded to the questionnaires (on students’ self-reported cognitive self-reliance and on parents’ characteristics and family background respectively). Chi-square statistic was used to analyse the data. The results showed that there was no significant relationship between mothers’ occupation and the students’ level of cognitive self-reliance (x2 = 9.61, p > 0.05); however, there was a significant relationship between fathers’ occupation and the students’ level of cognitive self-reliance (x2 = 28.83, p = 0.000); there was a significant relationship between mothers’ educational attainment and students’ levels of cognitive self-reliance (x2 = 28.83, p = 0.000), whereas fathers’ educational attainment did not show any significant relationship (x2 = 12.30, p > 0.05); there was a significant relationship between students’ level of cognitive self-reliance and parents’ degree of religiosity (x2 = 30.72, p < 0.05); family size was not significantly related to students’ levels of cognitive self-reliance (x2 = 10.16, p > 0.05), but family structure was related significantly (x2 = 15.12, p < 0.05). Based on the findings, recommendations were made among others that efforts should be made to support and improve mothers’ education as well as to enhance fathers’ involvement in children’s education. Schools should provide resources and counselling that cater to the unique needs of different family configurations and should develop programmes on effective parenting strategies that promote self-reliance and autonomy among adolescents.