In 2004, prior to the launch of their 1-to-1 laptop program, the superintendent expressed some anxiety about the prospect of radically changing teaching and learning by issuing a laptop computer to every student and teacher. Although the concept was exciting, it carried big risks and would take time and thorough planning to execute well. Even with their conscientious approach to the 1-to-1 Laptop eLearning Initiative, surprises came their way. This article highlights six unanticipated developments that arose in the Pascack Valley Regional High School District in Montvale, NJ: (1) The Maintenance Program; (2) The Inventory and Repair-Tracking System; (3) Faculty Reaction to the 1-to-1; (4) Creativity Unleashed; (5) Managing Hardware and Software via a Wireless Network; and (6) Success Brings Program Value and Public Support.