When Braille Institute in Los Angeles conceived The Braille Challenge contest more than a decade ago, the goal was to create an innovative way to promote braille literacy. Now that more than 4,500 students over the last 12 years from across the United States and Canada have chosen to participate in The Challenge, it is safe to say that it has been a success. From a technological standpoint, until last year, The Challenge had been holding back from embracing digital technology. In the past, students were allowed to use manual braillers and cassette tape players. In 2011, the committee responsible for The Challenge (of which the author is director) finally took the first step toward using digital technology by requiring participants to use digital audio players instead of analog tapes. This transition gave a surprising sense of how wide of a gap remains between early adopters of new technology and those who have yet to embrace devices such as accessible MP3 players. It was also learned that in order to successfully bridge this gap, the most important thing to do is to ensure that teachers of visually impaired students are provided with relevant and easily digestible ways to learn how to use such new technology. In this article, the author describes how The Challenge serendipitously accelerated the use of digital audio players.