Whether online, offline, hybrid, distant, or even e-learning, recent developments in technology all over the world have changed the way learning and teaching is designed and delivered. Recently, some university consortia in the US announced that they would be offering large-scale online degree courses, for free. Irrespective of the repercussions of such an initiative, it seems very likely that the future of higher education will be online courses. In recognition of this reality, universities are providing continuous professional development to their faculty, particularly in the area of online teaching and learning. But the challenges are not only technical but cultural too. This chapter discusses the general requirements and challenges (both technical and cultural) that face a designer of an online or hybrid language program that is communicative, interactive, exciting, motivating and engaging for students. More specifically, the chapter details the road travelled by the author in designing and delivering a hybrid Intermediate 2 Swahili program in spring 2013 to American students at American University in Washington DC. The technical, technological, and cultural issues encountered by both the lecturer and the students are reviewed in the chapter.