Technological shifts make it more important than ever to consider the intersection of technology and disability. On the one hand, technology can help to empower people with disabilities by providing tools for more independence and access to opportunities. However, technologies and services often do not consider the needs of people with disabilities from the beginning of the design process, disempowering and excluding them from participation in today’s digital age. Looking at new and old issues in tandem helps to both give perspective on the significant changes of the digital world and keep connected with and able to learn from history. Today, some of the most significant catchphrases in the world of technology are artificial intelligence, machine learning, the Internet of Things, and automation. Throw in an autonomous vehicle, some virtual reality, and some blockchain-based cryptocurrency, and we have the technology sector of tomorrow. Artificial intelligence (AI), the big data product comprised of machine learning and natural language processing, is having a moment. As we look toward the future, we must think carefully and critically about the core questions and key themes that exist when technology meets disability and marginalization so that we do not simply replant the same seeds. How can technology be used to affect the lives of people with disabilities positively? What problems is technology currently causing? How can we innovate in the design of new technologies, in the design of technology processes, and in the design of governance structures to allow and encourage innovation and mutually beneficial interactions regarding disability and technology?