Gob-side roadways driven along the floor while retaining top coal in thick soft coal seams are prone to instability under strong mining-induced dynamic loading. To clarify the instability mechanism and develop an effective control method, the 1609 return airway of Jiulishan Mine was investigated using field survey, borehole imaging, FLAC3D numerical simulation, industrial testing, and field monitoring. The results show that, under the combined effects of large mining height, insufficient filling of the gob by the caved immediate roof, weak retained top coal, and low coal strength, shear failure planes tend to develop within the narrow coal pillar and extend from the gob-side roof toward the floor. Once the dominant shear plane cuts through the pillar, the overall bearing structure is destroyed, leading to shear slip, asymmetric rib deformation, roof subsidence toward the coal-pillar side, and rib–roof coupled instability. Based on a multi-index evaluation of pillar load-bearing capacity, plastic zone development, stress concentration, roadway deformation, and coal recovery, a 3 m coal pillar was determined as the rational width. A coordinated “narrow coal pillar + cross-rib anchorage” scheme was proposed, and field verification confirmed its effectiveness in controlling roof separation, roadway surface displacement, and internal surrounding-rock damage.