Despite the early emergence of pointing, children are generally not documented to produce iconic gestures until later in development. Although research has described this developmental trajectory and the types of iconic gestures that emerge first, there has been limited focus on iconic gestures within interactional contexts. This study identified the first 10 iconic gestures produced by five monolingual English-speaking children in a naturalistic longitudinal video corpus and analysed the interactional contexts. We found children produced their first iconic gesture between 12 and 20 months and that gestural types varied. Although 34% of gestures could have been imitated or derived from adult or child actions in the preceding context, the majority were produced independently of any observed model. In these cases, adults often led the interaction in a direction where iconic gesture was an appropriate response. Overall, we find infants can represent a referent symbolically and possess a greater capacity for innovation than previously assumed. In order to develop our understanding of how children learn to produce iconic gestures, it is important to consider the immediate interactional context. Conducting naturalistic corpus analyses could be a more ecologically valid approach to understanding how children learn to produce iconic gestures in real life contexts.