Language interaction has been shown to positively impact second language development (Long, 1996). However, whereas research that examined interactionist approaches to second language acquisition (Gass & Mackey, 2006) has meticulously studied how different factors in the interaction (interactional context, type of task, etc) may affect L2 learners' outcomes (Ziegler, 2016), telecollaboration research has not (Dooley, 2017), mostly because this kind of research is often embedded into a course curriculum, and factors such as type of task vary widely across the board (O'Dowd & Waire, 2009). The current study aims to contribute to telecollaboration research by examining type of task, as well as the potential preparation L2 learners may engage in before participating in videoconferencing sessions. Twenty Spanish L2 learners completed two videoconferencing sessions (framed as two different tasks) with Spanish native speakers, using TalkAbroad. L2 learners' perceived learning gains and preparation data before participating in the videoconferencing component was obtained via an English guided self-reflection assignment completed post-interaction. Results suggest that learners experienced language (i.e., vocabulary) and personal learning gains (cultural knowledge and an increase in confidence), but how many learners, and how they prepared for these two different sessions differed depending on the task.