The Wellington Range region, in far Northern Australia, provides a remarkable record of cultural encounter. Cathedral-sized rock art galleries include contact imagery referencing Macassan and European visitors while lithic artefact assemblages echo social mobility between Indigenous groups occurring from at least the mid Holocene period. In this paper, we continue the trajectory of archaeological research in this region by examining community entanglement over the longue durée, focusing on the Mayarnjarn rock-shelter complex. Specifically, and following advice from traditional custodians, the authors complement archaeological excavation results with reflections on interactions between Traditional Mawng speaking Owners and archaeologists occurring during the 2016 and 2018 field seasons. This paper provides a cultural chronology built around both OSL and radiocarbon dates, a first for the region, indicating site activities dating from the terminal Pleistocene. An increase in exotic artefacts and presence of paintings belonging to a pan-Arnhem land rock art tradition suggests widening social networks during the Holocene. Insight into the nuanced nature of interactions, also the role of animate objects as relationship referents, emerge through ethnography and experience as the field season unfolds.