In 2002, the first in a series of working conferences was held as a collaboration between the counseling service of Bennington College and the Austen Riggs Center's Erikson Institute. The title of the first conference was "The Escalating Use of Medications by College Students: What Are They Telling Us, What Are We Telling Them?". It was meant to provide a space to explore the meaning and context of this phenomenon. The primary contexts examined were the student's familial/cultural context and then the institutional context from which the counseling staff was attempting to respond to the student. This paper describes that initial conference and the emergent themes over the next few years.