Educational technology offers unique affordances as a learning tool and delivery system for enhancing and personalizing instruction. Over the past two decades, efforts by school districts and states to infuse technology into everyday K-12 education through one-to-one laptop initiatives have rapidly proliferated. In this paper, I examine such initiatives from studies in the literature and from my own research, starting with the Apple Classroom of Tomorrow in the mid-1980's and continuing today with comprehensive mixed-method evaluations in school districts. Drawing from this work, I focus on several themes that create both challenges and opportunities for technology infusion to occur in more effective and sustainable ways. These include: (a) conceptualizing technology as an educational tool and delivery system, not as a "treatment" in itself; (b) defining and communicating to stakeholders what proximal and long-term outcomes the technology initiative is (and is not) expected to promote; (c) not over-promising impacts on student achievement on standardized assessments where technology applications are directed primary toward other educational goals; and (d) conducting ongoing evaluation studies to provide evidence of program implementation progress and effectiveness at different phases of the initiative.