From the outset of the author's career in adult education 20 years ago, teachers, program directors, and policymakers were touting the use of technology to improve student learning (and professional development for teachers as well). Unfortunately, however, despite islands of excellence here and there, the introduction of computers and digital technology into adult education has often failed to live up to the loftier expectations proponents anticipated. Technology is expected to overcome the pervasive lack of investment in the adult education system, or the significant barriers facing learners when it comes to accessing and using technology--or that somehow the technology itself will make those problems go away. The investments (in teachers, professional development, technical support, and basic infrastructure) that are needed to support the use of technology are underestimated. These challenges should dissuade people from developing these tools, but they should be more discerning about the tools used and more realistic about the challenges of deployment. The author addresses some of these challenges, including access to broadband, device access, the role of schools and programs, space and time for learning, meaningful interactivity, creativity and agency, and technology as a compensatory tool.