Confidence helps sustain people to use their mobile technology devices in daily life. However, there is little research that discusses how to build confidence among older adult users when starting to use technology and broadening their existing technology use. To understand older adults' confidence in technology use, we conducted an exploratory study over six months with ten participants in a residential care setting. We investigated the relationship between confidence, experience, and personal interest to use technology in their embracing of technology. Our findings show that confidence can be gained from positive experiences of use and that confidence helps with subsequent technology engagement. Positive experiences encourage further and broader experimentation with their own devices. Activities using technology to support personal interests provide great motivation for participants to expand the use of their mobile technology devices. We provide guidance on a facilitation process that is clear and step-wise to contribute to building confidence of users in residential care settings.