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Recent studies demonstrate that inadequate undergraduate advising often contributes to engineering students switching out of their majors. In this paper we present findings from a project undertaken to design and implement a web-based advising system for first-year engineering students. The advising system, AdWiki, has been accessed over 6425 times by over 1260 students since its full implementation. AdWiki was created to address three major issues in advising: (1) heavy faculty advising responsibility in the department, (2) lack of appropriate faculty rewards for time and effort spent on advising, and (3) inefficient uses of advising resources. Were recognized a need for a technology-based solution, one that was useful, usable, and sustainable. To achieve this objective, we turned to theoretical literature on the design and use of technology and approached our project through the socio-technical perspective. This perspective recommends a holistic and humanistic approach to design, where technology is just one element of a larger system. AdWiki has seen tremendous usage since full deployment, which we believe is a result of our approach. In this paper, we discuss our theory-guided approach to system design and present assessment and usage data to support our process and findings.