This thesis presents a study on semi-analytic methods for modeling waveguides with complex-shaped boundaries. The electromagnetic fields inside inhomogeneous and anisotropic media are solved via cylindrical harmonics as a basis for other numerical approaches, including the regular perturbation method (RPM), the cavity-material perturbation method (CMPM), and the point-matching method (PMM). The novel semi-analytic solutions we have explored here can be employed for the analysis of wireless communication along tunnels and boreholes as well as for the modeling of realistic logging-whiledrilling (LWD) sensors and their environments at low-frequency geophysical problems. We studied the potential of the RPM when combining it with the transformation optics (TO) principles to analyze an eccentric coaxial waveguide filled with anisotropic materials. Furthermore, we have extended the classical CMPM proposed by Harrington to handling anisotropic media for solving the cutoff wavenumbers of the modal fields in the same eccentric coaxial waveguide in an approximated but numerically efficient manner. Another perturbation solution is proposed here and combines the low-order corrections from RPM into the CMPM for providing high-order corrections to the cutoff wavenumbers of the modes supported in this guide. A mathematical formulation of a semi-analytic point-matching method for solving more complex anisotropic-filled waveguides with an arbitrary number of layers is also presented. An improved version of this method is introduced for modeling noncircular multi-layered cylindrical guided structures. Such point-matching-based solutions represent good alternatives to brute-force approaches such as finiteelement and finite-difference methods and motivate further investigations. We present a series of validation results showing the accuracy, efficiency, and potential limitations of the explored methods.