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This article is a status report of the on-going efforts of the DiLiterati Group (funded by Singapore’s Ministry of Education and led by Ravi Sharma) to investigate the role of digital literacies in fostering sustainable development. In this research, we are trying to investigate how the knowledge disparities could be bridged with digital literacy and whether the resultant “level playing field” will generate greater contributions of national wealth and a more equitable sharing of it. This culminated in the synthesis of a Digital Literacy Maturity Model. A quantitative approach to sense-making did not reveal much support for the model we had anticipated. Therefore a procedure to delve deeper into the qualitative and contextual was formulated to frame “narratives” that suggest “lessons learnt” and “best practices” from economies that have demonstrated successful sustainable growth and development. To test the efficacy of the procedure, Singapore and Hong Kong were selected as pilot subjects of interest.