This paper presents the results of a detailed theoretical study of the bending properties of original all-glass leakage channel microstructured optical fibers (LC MOFs) over a bending radius range from 3 cm to 11 cm. These LC MOFs contain two layers of fluorine-doped silica glass elements with reduced refractive index, different diameters, and different distances between them. We determined the spatial distributions of the electric field components of different modes in addition to the usual parameters such as effective refractive indices, bending losses, and spatial intensity distributions. A detailed analysis showed that three modes for each polarization have to be considered to correctly calculate the bending losses. Two pairs of these three modes couple in two distinct bending radius ranges, specifically near 3.68 cm and near 5.95 cm, and the mode coupling in these pairs is resonant. The resulting bending losses of the LC MOF for two polarizations are very close to each other and have two maxima at bending radii of 3.68 cm and 5.95 cm. However, the nature of these maxima is not resonant; they are caused by the combined influence of all three modes, each of which has specific dependencies of losses and other parameters on the bending radius that exhibit quasi-resonant behavior near the corresponding bending radii.