How professional development is delivered in today's networked world has shifted greatly, and research into online spaces of learning is growing. Numerous questions, however, remain regarding how online spaces can be leveraged to foster meaningful conversations that address current critical educational issues. This qualitative study examines the complex nature of questions and discussions that emerge in and across a critical literacy Web seminar project, Global Conversations in Literacy Research (GCLR), a series of open-access Web seminars that engage global audiences in discussions around literacy theory, research, and practice. This article addresses the following research questions: (1) When initial questions are posed, how are the discussion questions taken up by participants and speakers in this critical literacy Web seminar project? (2) What learning occurs in online professional development spaces grounded in critical literacy? [This article was written with the GCLR Research Team: Aram Cho, JiHye Shin, Christi Pace, MyoungEun Pang, MandiSena, & JinKyeong Jung.]