A dynamic hybrid Reynolds-averaged Navier-Stokes (RANS)-Large Eddy Simulation (LES) modeling framework has been investigated and further developed to improve the Computational Fluid Dynamics (CFD) prediction of turbulent flow features along with laminar-to-turbulent transitional phenomena. In recent years, the use of hybrid RANS/LES (HRL) models has become more common in CFD simulations, since HRL models offer more accuracy than RANS in regions of flow separation at a reduced cost relative to LES in attached boundary layers. The first part of this research includes evaluation and validation of a dynamic HRL (DHRL) model that aims to address issues regarding the RANS-to-LES zonal transition and explicit grid dependence, both of which are inherent to most current HRL models. Simulations of two test cases—flow over a backward facing step and flow over a wing with leading-edge ice accretion—were performed to assess the potential of the DHRL model for predicting turbulent features involved in mainly unsteady separated flow. The DHRL simulation results are compared with experimental data, along with the computational results for other HRL and RANS models. In summary, these comparisons demonstrate that the DHRL framework does address many of the weaknesses inherent in most current HRL models. Although HRL models are widely used in turbulent flow simulations, they have limitations for transitional flow predictions. Most HRL models include a fully turbulent RANS component for attached boundary layer regions. The small number of HRL models that do include transition-sensitive RANS models have issues related to the RANS model itself and to the zonal transition between RANS and LES. In order to address those issues, a new transition-sensitive HRL modeling methodology has been developed that includes the DHRL methodology and a physics-based transition-sensitive RANS model. The feasibility of the transition-sensitive dynamic HRL (TDHRL) model has been investigated by performing numerical simulations of the flows over a circular cylinder and a PAK-B airfoil. Comparisons with experimental data along with computational results from other HRL and RANS models illustrate the potential of TDHRL model for accurately capturing the physics of complex transitional flow phenomena.