The selection and use of appropriate energy efficient technologies, systems or devices present a challenge for organizations across diverse supply chains. The list of activities currently being trialed and promoted is extensive, with new technologies and methods constantly emerging. However, the degree to which even proven energy efficiency measures are adopted by logistics practitioners varies dramatically. Such adoption variations are present despite the support of company or governmental policies. This paper aims to explain operational decisions in the adoption of energy efficiency measures, specifically in those activities surrounding transportation, through the use of “customers’ purchasing behaviors”, as defined by the Dynamic Alignment framework. Two studies are presented. The first one, conducted in Argentina with national and international companies across a range of industrial sectors, provide rich insights into why study participants (hands on operational) may deviate from stated organizational sustainability goals. The second study is currently being performed in Colombia, and illustrates how the Dynamic Alignment framework can be used to understand how policies in support of energy efficiency may be received by market participants, and potential strategies that could encourage or enhance adoption could be devised.