Online learning is swiftly transforming higher education and placing novel demands on adult learners. Adults are forced to navigate new territories in the ways they self-direct their learning and self-reflect on their relationships with technology, particularly through the alone/together paradox (Turkle, 2011) of technical connectedness. While the literature concerning online learning is vast, missing is the constructive-developmental perspective (Kegan, 1982, 1994) on learning with and through technology. The incongruence between the demands of online learning and the cognitive and reflexive capacities of most adult learners poses an exigent problem. Using data from in-depth, qualitative interviews and polarity maps with seven graduate students spanning socialized and self-authored ways of knowing, this study sought to understand how adults construct meaning, develop, and grow within the context of an online, structured, educative space. Three areas of inquiry guided this study: (1) How does an adults developmental stage, or way of knowing, shape his or her online learning experience? (2) How do adults at varying developmental stages describe and understand the alone/together paradox in the online learning environment? (3) How, if at all, may an online, structured, educative space foster developmental shifts that will help adults meet the unique demands of online learning? The findings of this study describe how developmental capacities influence adults online learning experiences and their understandings of the alone/together paradox. The findings also describe how the online environment acts as a holding environment for adults at the socialized and self-authored stages of development. These findings suggest that the online learning environment is a catalyst for growth and development, for those who are ready, by virtue of manifesting the alone/together paradox. This study also discusses growing edges for socialized and self-authored knowers in the online environment and suggests developmentally diverse online practices to engage adults in the complexity of the alone/together paradox.