In her seminal treatise on African oral literature, Ruth Finnegan asserts that riddles in traditional African societies are of minor interest, used mostly for childish entertainment rather than for serious consideration. While it is true that riddles are among the oral arts performed mainly by children, this oral art form occupies a much more important and complex role in traditional African societies. In this paper, I will use examples from communities across the continent, to examine the structure and form of types of African riddles. I will also discuss their use as a didactic tool as well as the important role they play as an indigenous form of cryptography employed to transmit important political messages and facilitate communication among initiates to certain secret societies. I conclude with a discussion of how modern social media such as Twitter, with its word limits and emphasis on concise and sometimes discreet expression (via subtweets) lends itself to riddling as employed in African societies.