Thirty years on, "Rutter's gap" remains a challenge for Aegean prehistorians. With a precision commonly overlooked by his critics, Rutter originally set out to draw attention to a lacuna in our knowledge of material from stratified sites in the Cyclades, or of Cycladic material exported elsewhere, at the end of the third millennium B.C.E. and to a consequent hiatus in our ability to trace how island culture and behavior shifted from the Early to Middle Bronze Age. Whether the "gap" represented a real cessation of activity, whether it might be reduced from both ends, and whether genuinely interstitial strata and material might one day emerge were left open to the future. That future is now here, and this article asks where we stand today. It reviews new evidence from the Cyclades, the paucity of which suggests that the problem is at some level real, and highlights shifts of emphasis in the temporal pattern of change suggested by fresh data. It explores how two subsequent explanatory models have fared against new information: first, the association with a horizon of climate-induced collapse, and second, an explanation in terms of the maritime transition from canoe-borne to sail-driven shipping. Lastly, a pan-Mediterranean perspective reveals the third millennium B.C.E. as a period of burgeoning island societies and long-range sea traffic, but one that also witnessed crises in several island cultures toward its end, under conditions of increasing external penetration.