The pairing of telecollaboration and focused instruction can lead to measurable gains in second language learners' pragmatic competence (Belz & Vyatkina, 2005, 2008; Vyatkina & Belz, 2006). This article examines speech act production in telecollaborative exchange, focusing on the requesting behavior of American learners of German for professional purposes as they interacted with German-speaking professionals in Germany via synchronous Web conferences. Drawing on quantitative and qualitative methods, the study investigated the effect of interaction with expert speakers and the implementation of focused instruction on learners' pragmatic development. Whereas quantitative analysis showed no change between experimental conditions, qualitative analysis of 4 learners' request production over the course of 4 online discussions revealed idiosyncratic developmental pathways and the emergence of a common strategy for managing participation in oral synchronous computer-mediated communication. The findings provide new insight regarding the nature of second language request production and confirm the utility of pragmatics instruction in telecollaboration. At the same time, the study calls for more refined analytical tools when investigating language development in extended telecollaborative discourse.