The theme for the 2006 Transportation Association of Canada (TAC) Annual Conference, “Transportation without Boundaries” creates an image in the minds of most transportation professionals of what we would like to achieve within the next decade. However, our pragmatic side says there are institutional barriers that need to be breached and entrenched work cultures that must be changed in order to attain such a vision. A computer-based training (CBT) program is helping transportation agencies in Canada and the United States (US) transcend traditional training boundaries of time and distance to improve winter maintenance operations. The CBT is being used in both individual and conventional group training modes. It is most effective and efficient as an individual self-paced instruction program. Both the group and individual modes are structured to serve a wide range of learning abilities in the student population, including those with challenges such as dyslexia or hearing loss. In an effort to reach field forces more effectively, the American Association of State Highway and Transportation Officials (AASHTO) launched an Anti-Icing/Road Weather Information System (AI/RWIS) CBT into the winter maintenance training arena. Over 90% of US snow-belt states, three provinces and numerous cities in both countries have purchased the CBT. This paper describes how the AI/RWIS CBT is being utilized in both countries and underscores the valuable lessons learned from successful and not-so-successful deployments. It also shows how institutional barriers were breached, entrenched work cultures changed, and how recent research is being incorporated into the instructional content to ensure that training material stays current.