Using information and communication technologies (ICTs) can improve older adults’ quality of life. ICT use is associated with decreased feelings of loneliness and depression, along with increased feelings of independence and personal growth. However, limited access and low technological self-efficacy are key reasons why some groups, especially older adults, are excluded from being fully engaged in the digital world. In this study, we focus on older adults’ technological self-efficacy, which is related to their actual use of technology and the second level digital divide. Specifically, we examine: (a) how older adults decide to use a new technology, tablet computers; (b) how they conquer the barrier of technological self-efficacy through using tablets; and (c) the impacts of using this new technology in their lives. Twenty-one in-depth interviews were conducted with older adults residing in independent living communities in a medium-sized city in the Deep South region of the United States. Observational and enactive learning played important roles for older adults in using tablets. Seeing others use tablets, getting recommendations from family members, or having tablets given to them were the primary reasons they started to use tablet computers. The ease of use feature of tablets helped solve the problem of lacking technological self-efficacy. Using tablets helped increase a sense of connectedness. Tablet computers may be one way to increase digital inclusion among older adults.