This working paper describes an exploratory research investigation of the factors affecting the success of digital literacy skills training offered by local community organizations, such as public libraries. The study investigates how public libraries and other community-based organizations can best deliver the digital literacy initiatives they provide to the communities they serve. Case studies of two public libraries and five community organizations in the Greater Toronto and Hamilton Area (Canada) were carried out. Data collection comprised: a) one-on-one interviews with administrators, instructors, and people who received training; b) the analysis of training documents; c) observations of training sessions; and d) a survey administered to clients who participated in these training sessions. Qualitative data analysis techniques identified a variety of factors that shape digital literacy training success. These factors include: i) organizing and training staff; ii) acquiring sustainable funding; iii) reaching marginalized populations; iv) offering training at convenient times to end-users; v) marketing the training; vi) sharing and adopting best practices; and, vii) collecting and analyzing performance measurement data. How these factors inter-relate, and how these factors differ between different types of end-users and different types of local community organizations were explored. From these findings, recommendations for practice on how to run successful digital literacy training programs are provided. Ultimately, the factors identified in this study will guide the development of several survey instruments that will be administered to public libraries (both administrators and clients) across Canada in order to gain not only a national picture of digital literacy initiatives offered by public libraries and other community organizations, but also to better understand how organizational and end-user considerations surrounding these initiatives impact digital literacy training success