The purpose of this paper is to qualitatively examine the relationship between problem based learning, authentic assessment and the role of community in fostering learning in digital contexts. The authors used "Digital Moments" to create a meaningful learning environment and build the online class community. They then collaboratively developed assessment strategies and tools with students following problem-based learning methodologies. Given that the pace of information is rapid and changing, the authors argue that online learning must occur in a context that embraces these three concepts: 1. Students must be empowered through PBL to choose real world tasks to demonstrate their knowledge, 2. Students are allowed to choose the modality to represent that knowledge and participate in designing the tools for assessing that knowledge and 3. They do so in a supportive online community built through the sharing of Digital Moments. The paper chronicles the interconnection between problem based learning, authentic real world assessment tasks and a supportive online community. This resulted in developing learner autonomy, improving student engagement and motivation, greater use of meaningful self and peer assessments and shared development of collective knowledge. Further to this, it builds a foundation from which authentic assessment, student ownership of learning and peer support can occur in an ongoing way as learners make the important shifts in power to owning their learning and becoming problem-based inquirers in future courses. As a result, in order to fully embrace the online learning environment, we cannot limit ourselves to simple text based measures of student achievement. Stepping into this brave new world requires innovation, creativity and tenacity, and the courage to accept that as the nature of knowledge has evolved in the digital landscape, so must our means of assessing it.