Settling of non-spherical particles in a stratified fluid exhibits complex dynamics in a low-to-moderate inertia regime. Although this process is involved in a wide variety of phenomena in natural fluid systems, its fundamental mechanisms are still unexplored. Understanding of particle settling in microscale is particularly important to explain challenging problems associated with ecological and biogeochemical processes in the ocean due to the delayed settling of particulate matter at pycnoclines. Here, I explore interactions between disk-shaped particles and a stratified fluid with a density transition. By laboratory experiments, I demonstrate that the settling dynamics of the disk crossing a density transition are tightly coupled with the wake structure evolution, and I observe for the first time in a two-layer ambient configuration a bell-shaped structure that forms on a jet after the wake has detached from the particle. Furthermore, I identify hydrodynamic conditions for the variations of settling velocity and particle orientation instabilities. These findings shed light on particle settling mechanisms necessary to explain dynamics of marine particles such as plankton, faecal pellets, and microplastics and may improve the estimation methods of sedimentation processes in various areas of earth sciences and engineering.