This article examines the contextual challenges that characterize the video on demand (VOD) market in Africa. It provides critical analysis of the creative strategies employed by Nigeria-based streaming services to navigate the peculiar business environment on the continent. This research is on the background of the poor Internet infrastructure and economic divides in many African countries including Nigeria. Streaming services operating in these markets must understand a context where Internet access is complicated on the levels of availability and/or affordability, including significant lack of confidence in e-payment facilities. All these, together with epileptic power supply and poor standard of living, indicate that streaming services must innovate to capture subscribers within the continent. Despite the harsh operational environment, streaming services in Nigeria have continued to increase in number within the past 5 years. This is attributed to the transnational reach of the streaming services as they are patronized by Africans in diaspora across the globe, while they also enjoy popularity within African countries. This article specifically focuses on the innovative strategies employed by Nigerian streaming services to operate within their African markets in the context of their peculiar challenges. In so doing, it extends extant scholarship about Internet-distributed video using the African context. This article is situated within the Media Industry Studies framework and draws from semi-structured interviews with 7 streaming executives in Nigeria and 10 creative professionals in the Nigerian Video Film Industry (Nollywood). It also relies on desk research of press reports, industry publications, as well as the interfaces of streaming portals. This article underscores the necessity of contextualized research with the digital turn in video distribution. Through contextualized analysis of VOD market realities in a less studied terrain like Africa, it aligns with scholarly call to expand theories of Internet-distributed video to marginal contexts.