Marine cold-air outbreaks (CAOs) occur in the postfrontal sector of midlatitude storms, usually accompanied by dry intrusions (DIs) shaping the free-tropospheric (FT) air aloft. Substantial rain initiates overcast to broken regime transitions in marine boundary layer (MBL) cloud decks that form where cold air first meets relatively high sea surface temperatures. An exemplary CAO in the northwest Atlantic shows earlier transitions (corresponding to reduced extents of overcast clouds) closer to the low pressure center. We hypothesize that gradients in the meteorological pattern imposed by the prevailing DI induced a variability in substantial rain onset and thereby transition. We compile satellite observations, reanalysis fields, and Lagrangian large-eddy simulations (LES) translating along MBL trajectories to show that postfrontal trajectories closer to the low pressure center are more favorable to rain formation (and thereby cloud transitions) because of 1) weaker FT subsidence rates, 2) greater FT humidity, 3) stronger MBL winds, and 4) a colder MBL with reduced lower-tropospheric stability. LES confirms the observed variability in transitions, with substantial rain appearing earlier where there is swifter reduction of cloud condensation nucleus (CCN) concentration and increase of liquid water path (LWP). Prior to substantial rain, CCN budgets indicate dominant loss terms from FT entrainment and hydrometeor collisions. LWP-enhancing cloud thickness increases more rapidly for weaker large-scale subsidence that enables faster MBL deepening. Mere MBL warming and moistening cannot explain cloud thickness increases. The generality of such a DI-imposed cloud transition pattern merits further investigation with more cases that may additionally be convoluted by onshore aerosol gradients.