Parental and students’ expectations on the educational achievement of the latter have been highlighted in the literature as proper proxies for students’ forthcoming performance and high school track elections. In this research we intend to measure the effect of these expectations on students’ performance accounting for the existence of endogeneity, due to the reciprocal relationship between the expectations of parents and students and their correlation with unobservable variables conditioning students’ achievement. A rich dataset containing information on Andalusian parental and students’ socio-economic characteristics, expectations, parental involvement interactions and academic performance variables is used to conduct the empirical analyses. Our results show that the agreement of parental and students’ expectations presents a positive influence on students’ achievement and the likelihood of selecting a high school track. In addition, parental expectations have been found to be dependent on family socio-economic background, what supports the argument of the persistence in Andalusia of strong barriers to socioeconomic mobility. In the view of these results, we suggest policy interventions as, e.g., fostering the participation of both parents and students on university and professional orientation in early moments of secondary education, so they could have complete and symmetric information to set their expectations on realistic basis.