According to most memory theories, encoding involves continuous communication between the hippocampus and neocortex, but recent work has shown that key moments at the end of an event, called event boundaries, may be especially critical for memory formation. We sought to determine how communication between the hippocampus and neocortical regions during the encoding of naturalistic events related to subsequent retrieval of those events and whether this was particularly important at event boundaries. Participants encoded and recalled two cartoon movies during fMRI scanning. Higher functional connectivity between the hippocampus and the posterior medial network (PMN) at an event's offset is related to the subsequent successful recall of that event. Furthermore, hippocampal-PMN offset connectivity also predicted the amount of detail retrieved after a 2-day delay. These data demonstrate that the relationship between memory encoding and hippocampal-neocortical interaction is dynamic and biased toward boundaries.