This paper investigated the digital literacy acquisition process among vulnerable adults and describes how a tutor-facilitated learning environment helped these individuals bridge the digital divide. Data collected from six sites over the course of a year include field notes, learner and tutor interviews. Analyses involved an inductive coding procedure. As new patterns emerged, inductive procedures were used to revise the coding scheme in order to capture themes that emerged. Analysis provided insights into the challenges faced and how those challenges were addressed by learners, tutors, and the program.