With the rapid development of technology in medical education, orthopaedic educators are recognizing that the way residents learn and access information is profoundly changing. Residency programs are faced with the challenging problem that current educational methods are not designed to take full advantage of the information explosion and rapid technologic changes. This disconnection is often seen in the potentially separate approaches to education preferred by residents and orthopaedic educators. Becoming connected with residents requires understanding the possible learning technologies available and the learners' abilities, needs, and expectations. It is often assumed that approaches to strategic lifelong learning are developed by residents during their training; however, without the incorporation of technology into the learning environment, residents will not be taught the digital literacy and information management strategies that will be needed in the future. To improve learning, it is important to highlight and discuss current technologic trends in education, the possible technologic disconnection between educators and learners, the types of learning technologies available, and the potential opportunities for getting connected.