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The impact of extratropical transition (ET) on tropical cyclone (TC) tornadoes is not fully understood with no prior tornado climatologies for ET cases. Hence, this study investigates how ET impacts tornadoes and convective-scale environments within TCs using multidecadal tornado and radiosonde data from North Atlantic TCs. This research divides ET into three phases: tropical (i.e., pre-ET), transition (i.e., during ET), and extratropical (i.e., post-ET). These results show that the largest portion of tornadoes occurs before and during ET, with the greatest frequencies during ET. As TCs progress through ET, tornado location shifts north and east in the United States but farther south or more strongly downshear right relative to the TC center. Tornadoes also tend to occur later in the day and are more likely to be associated with greater damage. Evaluation of radiosondes shows that the downshear-right quadrant of the TC is frequently the most favorable for tornado production, with sufficient entrainment CAPE (ECAPE) and strong storm-relative helicity (SRH). Specifically, the downshear-right quadrant shows slower decreases in ECAPE (associated with synoptic-scale cooling and drying) and increased SRH and associated lower-tropospheric vertical wind shear through ET, relative to the other quadrants relative to the deep-tropospheric (i.e., 850–200-hPa) vertical wind shear vector. These results inform the physical model and prediction of ET-related TC structure, both in terms of their convective-scale environments and subsequent hazard production.