Higher education is a major driving force of transformation. To achieve this, higher educational attainment expectation among adolescent learners is critical. In order to clarify why it is challenging for so many black South African adolescents to pursue higher education using the little available facilities and resources, this study analyzed educational expectation factors in transforming higher education. This study adopted a quantitative research approach using the descriptive design of correlation type in other to explore variables such as parental engagement, academic self-efficacy and school connectedness on educational expectation of higher school adolescents in Kwa-Dlangezwa in South Africa. A total of 100 participants were selected as sample using simple random sampling with average mean age of 14 years (SD= 9.31). A structured questionnaire consisting of parental engagement, academic self-efficacy, school connectedness and educational expectation was used to collect data. Three research questions were asked and answered using Multiple Regression and Pearson Product Moment Correlation Statistical tools. The result revealed that educational expectation could be achieved by parental engagement, academic self-efficacy, and school connectedness. It was concluded that if educational system will be transformed for sustainable development, factors such as parental engagement, academic self-efficacy, and school connectedness should be given adequate consideration.