The Atlantic Tradewind Ocean-Atmosphere Mesoscale Interaction Campaign (ATOMIC) took place in January-February 2020. It was designed to understand the relationship between shallow convection and the large-scale environment in the trade-wind regime. Lagrangian large eddy simulations, following the trajectory of a boundary-layer airmass, can reproduce a transition of trade cumulus organization from “sugar” to “flower” clouds with cold pools, observed on February 2-3. The simulations were driven with reanalysis large-scale meteorology and ATOMIC in-situ aerosol data. During the transition, large-scale upward motion deepens the cloud layer. The total water path and optical depth increase, especially in the moist regions where flowers aggregate. This is due to mesoscale circulation that renders a net convergence of total water in the already moist and cloudy regions, strengthening the organization. An additional simulation shows that stronger large-scale upward motion reinforces the mesoscale circulation and accelerates the organization process by strengthening the cloud-layer mesoscale buoyant turbulence kinetic energy production.