Dryland ecosystems are frequently struck by droughts. Yet, woody vegetation is often able to recover from mortality events once precipitation returns to pre-drought conditions. Climate change, however, may impact woody vegetation resilience due to more extreme and frequent droughts. Thus, better understanding how woody vegetation responds to drought events is essential. We used a phenology-based remote sensing approach coupled with field data to estimate the severity and recovery rates of a large scale die-off event that occurred in 2014-2015 in Senegal. Novel low (L-band) and high-frequency (Ku-band) passive microwave vegetation optical depth (VOD), and optical MODIS data, were used to estimate woody vegetation dynamics. The relative importance of soil, human-pressure, and before-drought vegetation dynamics influencing the woody vegetation response to the drought were assessed. The die-off in 2014-2015 represented the highest dry season VOD drop for the studied period (1989-2017), even though the 2014 drought was not as severe as the droughts in the 1980s and 1990s. The spatially explicit Die-off Severity Index derived in this study, at 500 m resolution, highlights woody plants mortality in the study area. Soil physical characteristics highly affected die-off severity and post-disturbance recovery, but pre-drought biomass accumulation (i.e., in areas that benefited from above-normal rainfall conditions before the 2014 drought) was the most important variable in explaining die-off severity. This study provides new evidence supporting a better understanding of the "greening Sahel", suggesting that a sudden increase in woody vegetation biomass does not necessarily imply a stable ecosystem recovery from the droughts in the 1980s. Instead, prolonged above-normal rainfall conditions prior to a drought may result in the accumulation of woody biomass, creating the basis for potentially large-scale woody vegetation die-off events due to even moderate dry spells.