In recent reports the U.S. Department of Education issued a charge for 21st century skills for college and career readiness. With the ever-increasing societal influence of social media, educators had been grappling with the challenge of understanding the nature of multimodal literacy practices and supporting post-millennial youths’ literacy development. This mixed methods study captured youths’ multimodal literacy practices in the context of a digital storytelling community. Through the examination of a large repository of digital artifacts, the researcher analyzed the emergence of collective productivity rates and trending topics over a multiple year period. In order to investigate the meanings embedded in these artifacts, the researcher also conducted a multiple person case study to trace individuals’ meaning making through the construction of their digital artifacts. Eight youth from the ages of 7 to 13 participated in tasked-based interviews. Once the interviews records were transcribed, the youths’ practices, discourses, and artifacts were analyzed across cases. Through in-depth individual case analysis and cross-case analysis, the researcher identified the domains of meaning youth employed to create their projects. With the archive analysis and the multiple person case study, the researcher found collaboration as a dominant in the digital storytelling community culture. Gender was a key indicator of topic choices in the digital projects. The less experienced youth worked together on common projects. Their repertoires of practice expanded over time as they explored different subject matters and gained command over digital tool uses for creative purposes. Participants, who had more experience with multimodal literacies, were more likely to introduce new, more complex topics from virtual communities and social media platforms to the community. This study opened more opportunities for researchers to investigate ways multimodal literacies could have served other purposes such as cultivation of leadership, promote socioemotional resilience, and provide creative opportunities for youth from historically marginalized backgrounds.