We study the yielding transition in soft jammed materials under oscillatory shear, employing a novel methodology that combines rheological measurements with detailed dynamical observations. This method provides a comprehensive view of the intricate interactions between macroscopic mechanical behavior, mesoscopic deformation patterns, and microscopic dynamics during yielding. Our findings reveal two distinct yielding behaviors: at one end, a smooth, uniform transition, characterized by homogeneous strain fields, and Fickian, Gaussian microscopic dynamics; at the other, a sharp transition defined by pronounced shear banding, with the dynamics within shear bands being governed exclusively by the local strain, and exhibiting non-Gaussian, cooperative nature. The viscoplastic fragility emerges as a key macroscopic predictor of these intricate behaviors across micro- and meso-scales, providing a new perspective to understand and quantify ductile and brittle yielding in soft materials.