Online learning programs provide real time feedback and offer some degree of access to "real" oral communication, yet these platforms, for the most part, involve using the software in isolation. Though Rosetta Stone is designed for independent learning, the present study experiments with a model for implementing it as a collaborative tool for pair work. This article reviews several of Rosetta Stone's claims and reports on the experience of two language learners (the authors) working together to complete the first level Italian program. The authors/ language learners collaborated at one computer, and the data come from over 16 hours of audio recordings of their interactions and from independently written notes to document reactions, questions and observations that surfaced during the learning process. The analysis draws from Vygotsky's (1978) sociocultural theory, specifically learning as a social process and the corresponding value of collaborative learning. We highlight data that address four Rosetta Stone claims. Though our experience did not support all of those assertions, we successfully completed the learning unit. Working together mitigated some challenges and provided insight into the potential benefits of the collaborative use of software designed for single users.