We examine the relationship between Southern Ocean clouds and the dynamical controlling factors in three cases: 1) a poleward shift of the eddy-driven jet (on monthly timescales), 2) a composite of an extratropical cyclone (on daily timescales), and 3) a composite of an extratropical anticyclone (on daily timescales). In all three cases, observations and global climate models agree well on the magnitude and distribution of vertical velocity, lower tropospheric stability, and near-surface temperature advection. However, the models and observations differ on the relative importance of these factors in controlling the cloud field. In particular, models appear to overestimate the sensitivity of cloud cover to variations in vertical velocity and underestimate the sensitivity of cloud cover to variations in lower tropospheric stability and near-surface temperature advection. As a result, clouds are too bright along the cold front of an extratropical cyclone and are underestimated in extratropical anticyclones and in the region equatorward of a poleward jet shift.