The term “sustainability” has acquired an all-encompassing ambiguous aura, given that it touches on all facets of human endeavor. This paper, meant to provide a pedagogical framework for engineering education, starts by pointing out that since technology is an important and fundamental driver of current human development and inextricably interwoven into the societal fabric, the discourse on sustainability and sustainable development should evolve beyond its environmental and social origins. One should explicitly recognize the importance of technology in profundly shaping the discourse and not simply view it as an enabler of meeting preset equipment and system performance targets. In order to fragment the monolithic implied by the term “sustainability,” a categorization is then suggested ranging from individual products to wicked/complex adaptive systems as a fundamental level of separation. Subsequently, it is argued that the objective analysis of the multidimensional-spatial-temporal nature of sustainability, meant for the assessment of actionable design alternatives and for tracking the status of implemented measures, requires the definition of a small set of quantifiable umbrella capabilities and sub-attributes. The need to identify direct or surrogate parameters/variables and performance measures/metrics which characterize these sub-attributes is then discussed and mapped onto the application categories. Weighting and aggregating these sub-attributes to quantify the umbrella attributes necessarily introduce normative/aspirational preferences/biases of the various stakeholders, and this issue is also discussed. Finally, the two prevalent sustainability assessment frameworks, namely, the structure-based and the performance-based, are reviewed in terms of strengths and weaknesses and illustrative publications cited, and it is urged that more research be undertaken to synthesize these somewhat disparate approaches in dealing with natural, social, economic, political, and technological systems and organizations.