The application of technology in higher education has equally affected the learning process; thus, it is responsible for increasing student motivation and satisfaction. This paper is intended to discuss the satisfaction of students within the academic environment with Tech-Enhanced Learning from a constructivist and philosophical approach. Data collection occurred using surveys and semi-structured interviews conducted upon the responses of a collective 501 students from five universities. Descriptive analytics were conducted concerning the influence of four major variables-ease of use, engagement, learning enhancement, and satisfaction with digital resources-on student perceptions at large. The results indicate that though in general digital tools greatly enhance student satisfaction with their learning achievement results as well as quality issues are related to resource access and quality. The paper concludes that the more satisfied students are with their learning, the more it is interactive and communicative, thus aligning with the theory of communicative action. The support of public policy, therefore, with furor to establish an infrastructure tempts not to overshadow the teaching–learning process. It is the balanced approach of pedagogy between what is considered new and old that will see technology be used as a tool in creating meaningful and dynamic learning environments for students. Such findings, therefore, go to make a contribution to the ever-continuing discussions on philosophical aspects of education together with digital learning, implications for educators, government policymakers, and even stakeholders concerned with the venture.