This article describes a classroom project using one-to-one desktop videoconferencing to enhance the development of second language (1.2) oral skills. Eighteen university students worked collaboratively with expert speakers to complete task-based activities. The author gathered data from video-recording samples, reflections, and oral interviews to report the participants' experiences and examine the potential of desktop videoconferencing to support speaking skills. While this approach is effective in supporting collaborative learning and fostering L2 oral communication, learners with less sophisticated listening skills experienced difficulties comprehending native speakers. Native speakers' linguistic variations, including regionalisms and accents, also affected the degree of the interactivity. This study suggests three essential ingredients to maximize the potential benefits of desktop videoconferencing for language learning: (1) use of carefully designed tasks that engage learners, (2) appropriate selection of linguistic context, and (3) inclusion of sufficient network training. (Contains 7 notes.)