By the time the Roman empire reached its greatest extent, in the early decades of the second century ad, wooden barrels were a key part of a trade network that supported a complex extended economy. These objects do not, however, routinely survive in the archaeological record and very few sites have yielded large, multi-phase, assemblages for study. Although relatively rare, individual finds and assemblages have been found sufficiently regularly to allow us to consider barrel production and use during the Roman period. These objects can have complex cultural biographies from their original production to their final deposition. Current and previous research at Vindolanda, a Roman fort in northern Britain at the edge of the Roman empire, provides a context for reflection on these objects and their biographies. Emphasis is given to whether this material demonstrates repeated, possibly habituated, practices of adaption and recycling.