We overview various efforts within the DART Investigation Team’s Ejecta Working Group to predict the characteristics, quantity, dynamical behavior, and observability of DART impact ejecta. We discuss various methodologies for simulation of the impact/cratering process with their advantages and drawbacks in relation to initializing ejecta for subsequent dynamical propagation through and away from the Didymos system. We discuss the most relevant forces acting on ejecta once decoupled from Dimorphos’s surface and highlight various software packages we have developed and used to dynamically simulate ejecta under the action of those forces. With some additional software packages, we explore the influence of additional perturbing effects, such as interparticle collisions within true N-body codes and nonspherical and rotating particles’ interplay with solar radiation pressure. We find that early-timescale and close-proximity ejecta evolution is highly sensitive to some of these effects (e.g., collisions) while relatively insensitive to other factors. We present a methodology for turning the time-evolving size- and spatially discretized number density field output from ejecta simulations into synthetic images for multiple platforms/cameras over wide-ranging vantage points and timescales. We present such simulated images and apply preliminary analyses to them for nominal and off-nominal cases bracketing realistic total mass of ejecta and ejecta cumulative size–frequency distribution slope. Our analyses foreshadow the information content we may be able to extract from the actual images taken during and after the DART encounter by both LICIACube and Earth-vicinity telescopes.