Recurving tropical cyclones (TCs) undergoing extratropical transition (ET) may substantially modify the large-scale midlatitude flow pattern. This study highlights the role of diabatic outflow in midlatitude flow amplification within the context of a review of the physical and dynamical processes involved in ET. Composite fields of 12 western North Pacific ET cases are used as initial and boundary conditions for high-resolution numerical simulations of the North Pacific-North American sector with and without the TC present. It is demonstrated that a three-stage sequence of diabatic outflow associated with different weather systems is involved in triggering a highly amplified midlatitude flow pattern: 1) preconditioning by a predecessor rain event (PRE), 2) TC-extratropical flow interaction, and 3) downstream flow amplification by a downstream warm conveyor belt (WCB). An ensemble of perturbed simulations demonstrates the robustness of these stages. Beyond earlier studies investigating PREs, recurving TCs, and WCBs individually, here the fact that each impacts the midlatitude flow through a similar sequence of processes surrounding ET is highlighted. Latent heat release in rapidly ascending air leads to a net transport of low-PV air into the upper troposphere. Negative PV advection by the diabatically driven outflow initiates ridge building, accelerates and anchors a midlatitude jet streak, and overall amplifies the upper-level Rossby wave pattern. However, the three weather systems markedly differ in terms of the character of diabatic heating and associated outflow height, with the TC outflow reaching highest and the downstream WCB outflow producing the strongest negative PV anomaly.