Tropical cyclone (TC) rapid intensity change negatively impacts forecast error. Many studies have investigated rapid intensification, but fewer explore rapid weakening, particularly with aircraft observations due to fewer weakening TCs being flown. This study assesses factors contributing to the rapid weakening of Hurricane Lorenzo (2019) and the comparatively slower weakening of Hurricane Florence (2018) using aircraft observations and satellite-based products to enhance understanding of processes related to TC weakening. Intrusion of environmental dry air into Lorenzo's core under persistent moderate vertical wind shear, in conjunction with quickly decreasing SSTs, largely contributed to the TC's rapid weakening. Conversely, SSTs were higher and decreased more slowly along Florence's track, and dry air did not reach the TC's core. Confirming these processes with both aircraft and satellite observations implies that satellite analysis in the absence of reconnaissance could detect these features to some extent which may support future operational forecasting.