The escalation of complexity is a commonly cited benefit of coevolutionary systems, but computational simulations generally fail to demonstrate this capacity to a satisfactory degree. We draw on a macroevolutionary theory of escalation to develop a set of criteria for coevolutionary systems to exhibit escalation of strategic complexity. By expanding on a previously developed model of the evolution of memory length for cooperative strategies by Kristian Lindgren, we resolve previously observed limitations on the escalation of memory length by extending operators of evolutionary variation. We present long-term coevolutionary simulations showing that larger population sizes tend to support greater escalation of complexity than smaller ones do. Additionally, we investigate the sensitivity of escalation during transitions of complexity. The Lindgren model has often been used to argue that the escalation of competitive coevolution has intrinsic limitations. Our simulations show that coevolutionary arms races can continue to escalate in computational simulations given sufficient population sizes.