Drought is a complex natural hazard that is endemic to the Canadian prairies. The 1999–2005 Canadian prairie drought, which had great socioeconomic impacts, was meteorologically unique in that it did not conform to the traditional persistent positive Pacific–North American (PNA) pattern and west coast ridging paradigm normally associated with prairie drought. The purpose of this study is to diagnose the unique synoptic-scale mechanisms responsible for modulating subsidence during this drought. Using 30-day running means of the percent of normal precipitation from station data, key severe dry periods during 1999–2005 are identified. Analysis of the mean fields from reanalysis data shows that these dry events can be grouped into three upper-level flow categories: amplified warm, amplified cold, and zonal. Amplified warm cases match the traditional ridging paradigm, while amplified cold and zonal cases elucidate the fact that cold-air advection and downsloping flow, respectively, can also be important subsidence mechanisms during a Canadian prairie drought. In all, the 1999–2005 drought was more meteorologically complex on the synoptic scale than previous historic prairie droughts. Finally, a brief historical perspective shows that the drought was centered in 2001–02 and was not as severe as historical droughts, suggesting that societal vulnerability also played a substantial role in the impacts of the 1999–2005 drought.