There is convincing evidence that the learning environments digitalization of tools and equipment ultimately results in the speed and depth learning involvement of academia members, by raising attainment of each of the digital learning experiences. The majority of the research that was conducted on the topic of enhancing the digital skills of learners, which would ultimately lead to an increase in their active engagement, was conducted on students in primary and secondary education, leaving members of higher education outside of the scope of the study. Given the uninterrupted search for academic performance and innovation, the current research considers the technological changes that lead to the transformation of the traditional academic learning environments as previously known. The current paper considers the changes in the learners' engagement in the context of the dually digital transformation of the higher academic multi-institutional digitally-learning enhancements. An important factor to be considered regards the leadership evolution (in terms of teaching) that over time, led to a different speed contextual shift, according to its effectiveness, leading to higher or lower students learning (dis)engagement. The current manuscript aims to examine how the higher education digitalization levels could affect the student's learning engagement, under the close monitoring of the academia leadership styles practice. Data collection and analysis implied at first a qualitative approach by issuing an online-distributed survey that resulted in a number of 2272 valid responses. After performing structural equation modelling and proving a valid assessment tool, the analysis resulted into statistically proving the validity of two main hypotheses according to which students learning engagement has a positive effect on the practice of academic leadership. Additionally, results emphasized the fact that higher education digitalization has altogether a negative effect of students learning engagement. Consequently, the current study stresses on the importance of different peers' categories in the context of higher education institutions performance, with an emphasis on the different levels of students' engagement and the leadership styles evolution and practice, aspects uniformly developing within a continuously digitally transformation of the higher education environment.