With the rise of the older adult population worldwide and the rapid advancements in technology, it is becoming more important that senior citizens learn to use new technologies to remain active in society. To facilitate learning, technology-training programs should strive to capture and maintain a high level of engagement among older adults. In order to understand how to design effective technology-training programs, we examined the factors that affect the engagement of older adults as they learn to use technology. The first part of our study consisted of a survey that collected information about their preferences on various factors relating to learning engagement. Responders frequently indicated preferences for morning lessons in a familiar environment, often by teenage or older (over 50 years old) instructors, with a guided hands-on method. The second part of our study recorded the behavior of a group of older adults as they responded to different teaching delivery methods. The results indicated that an interactive lesson style was associated with a significantly higher level of engagement by participants. Older adults in interactive lessons asked more questions and retained course material at a higher rate than those subjected to video and written methods. In summary, these results suggest that many older adults prefer learning in the morning, in a familiar environment, by teenage or 50+ instructors, and with a guided hands-on method. Furthermore, an interactive learning method may increase engagement.