Loss of circulation while drilling is a challenging problem that may interrupt drilling operations, reduce efficiency, and increases cost. When a drilled borehole intercepts conductive faults or fractures, lost circulation manifests as a partial or total escape of drilling, workover, or cementing fluids into the surrounding rock formations. Studying drilling fluid loss into a fractured system has been investigated using laboratory experiments, analytical modeling, and numerical simulations. Analytical modeling of fluid flow is a tool that can be quickly deployed to assess lost circulation and perform diagnostics, including leakage rate decline and fracture conductivity. In this chapter, various analytical methods developed to model the flow of non-Newtonian drilling fluid in a fractured medium are discussed. The solution methods are applicable for yield-power-law, including shear-thinning, shear-thickening, and Bingham plastic fluids. Numerical solutions of the Cauchy equation are used to verify the analytical solutions. Type-curves are also described using dimensionless groups. The solution methods are used to estimate the range of fracture conductivity and time-dependent fluid loss rate, and the ultimate total volume of lost fluid. The applicability of the proposed models is demonstrated for several field cases encountering lost circulations.