Accurate prediction of tip leakage flow in compressors is crucial for improving aerodynamic performance, stability, and efficiency. However, conventional turbulence modeling approaches, including Delayed Detached-Eddy Simulation (DDES), often fail to capture the intricate unsteady flow phenomena in the tip region, such as the Kelvin-Helmholtz (K-H) instability and key vortex structures. This chapter examines the predictive capabilities and limitations of DDES in a high-loading cantilevered stator cascade with tip clearance, highlighting how insufficient turbulence resolution hinders the accurate representation of vortex breakdown, secondary leakage vortex formation, and subsequent loss mechanisms.To isolate the underlying causes of these shortcomings, a simplified three-dimensional model of a “multi-wall plus narrow gap” structure—representative of blade tip leakage conditions—is employed. Benchmarking against Large-Eddy Simulation (LES) results reveals that conventional DDES methods suppress K-H instability and fail to generate the necessary turbulence kinetic energy upstream of the leakage, thereby distorting the development of key flow features and altering the downstream total pressure loss distribution.Building on these insights, the Enhanced Delayed Detached-Eddy Simulation (EDDES) approach is introduced. EDDES alleviates the suppression of K-H instability and demonstrates improved predictive accuracy for tip leakage flow, capturing previously unresolved vortex structures and their interactions more faithfully. The subsequent application of EDDES to the compressor cascade, supported by comparisons with experimental data, confirms improved fidelity in predicting time-averaged aerodynamic parameters and detailed flow physics.In summary, this chapter establishes that refined DES-type methods, notably EDDES, can substantially enhance the accuracy of tip clearance flow simulations. These findings underscore the importance of proper turbulence resolution and instability capture in advancing both the understanding and practical design of high-performance compressor systems.