The purpose of this study was to establish whether and how authentic assessment activities and learner autonomy converged to productively engage both the teacher and learners in shared authenticity. The study employed case study methodology to investigate the phenomena within an online course in ICT designed for continuing professionals in education. The findings show that, through engaging with authentic assessment activities coupled with learner autonomy and formative processes, shared authenticity among the teacher and the students was inevitable. The shared authenticity was facilitated through a variety of ongoing and authentic assessment activities which through purposed formative processes created opportunities for active engagement that supported meaningful learning through prompting the students to apply their existing knowledge and connect what they were learning to their real-life professional practices and contexts. Learner autonomy that characterized these authentic assessment activities provided students with opportunities engage with activities that served their own learning goals and interests, which fostered self-regulatory dispositions and personalized learning. This in turn increased learners' engagement with meaningful experiences both individually and collectively as a learning community in ways that enhanced their ability to transfer their learning to real-life contexts.