This chapter explores the perceptions of 58 secondary school students regarding the design and implementation of a 7-week telecollaboration between English as a foreign language (EFL) learners in Mar del Plata, Argentina, and Spanish as a foreign language (SFL) learners in Pittsburgh, PA. The goal of the telecollaboration was to offer opportunities for the learners to develop their target language and intercultural learning skills in tandem. It was organized in three evidence-based stages that incorporated familiarization, collaboration, and reflection tasks. Students’ perceptions of challenges, benefits, and language and cultural learning gains were collected using two questionnaires that the learners completed at the beginning and end of the project. Both groups reported high levels of satisfaction with all aspects of the telecollaborative design and implementation and high overall appreciation for language and cultural learning gains. An in-depth analysis of their views uncovered three individual learner and teacher variables (L2 proficiency level; age; and teachers’ beliefs, communication styles, and collaboration skills) and four contextual variables (school characteristics, institutional support, use of class time, and telecollaboration format) that contributed to differences in the two groups’ appreciation of specific tasks and identification of benefits. The chapter concludes with pedagogical implications based on the findings.