Digital technology is used to improve the quality of life for the growing number of older adults in the United States, but it also exacerbated the digital divide between generations and regions. Digital literacy programs effectively designed for older adults have a potential to mitigate this issue; however, sustaining an effectively designed program can be a challenge due to practical constraints. This case study-mixed methods study examined effectiveness and challenges of implementing a digital literacy program that is designed with six instructional strategies known to be effective for older adults. Data sources included surveys and interviews from learners, instructors, including teaching assistants, and an administrator involved in the project throughout three implementation cycles at a regional library. Overall, participants reported enhanced confidence in using digital literacy domains and satisfaction towards the program. Various implementation challenges identified are aligned to the instructional strategies used. The study emphasizes the importance of developing and sustaining an inclusive and flexible digital education for seniors aimed to reduce the digital divide and promote their engagement in an increasingly digital society.