Recent critical focus on the anthropogenic arguments regarding the threats to the sustainability of biosphere highlight the role of engineering in maintaining the structural integrity of the human environment. However, the discipline of engineering is not without larger contextual and methodological problems that tend to undermine the perception of its benefit to society. These include tendencies towards utilitarianism, the irreconcilability of means vs. ends rationale, and the potential for difference-blind solutions to technical problems which ignore the possible harmful effects on the environment which extend beyond in-built cost-benefit analyses. This paper intends to reconcile scientific and humanistic views through a philosophical inquiry and argues that engineering is informed by a context that requires a counter-balancing perspective which accommodates holism, environmental compatibility, lateral and longer-term thinking as well as awareness of humanity, culture and society. Inclusion of humanities subjects within the engineering curriculum positively underscores human factors in technological problems and solutions and equips engineers with a cultural vocabulary and understanding. The argument will be made that a relationship between the humanities and engineering that resembles the Renaissance concept of the ‘artifex’ (or the attempt to harmonise the human and the technological) is both necessary and desirable for the enhancement, understanding and development of both disciplines. Furthermore, this paper demonstrates ways in which basic philosophical principles can contribute to critical thinking within the engineering discipline. This paper uses three humanities texts, Max Frisch’s Homo Faber (1959), Don de Lillo’s The Body Artist (2001), and the film Contact (1997) based on Carl Sagan’s book (1985) to problematise issues of technology and humanism and to explore the relationship of engineering to the humanities.