The initial post-buckling behavior of moderately thick orthotropic shear deformable cylindrical shells under external pressure is studied by means of Koiter’s general post-buckling theory. To this extent, the objective is the calculation of imperfection sensitivity by relating to the initial post-buckling behavior of the perfect structure, since it is generally recognized that the presence of small geometrical imperfections in some structures can lead to significant reductions in their buckling strengths. A shear deformation theory, which accounts for transverse shear strains and rotations about the normal to the shell midsurface, is employed to formulate the shell equations. The initial post-buckling analysis indicates that for several combinations and geometric dimensions, the shell under external pressure will be sensitive to small geometrical imperfections and may buckle at loads well below the bifurcation predictions for the perfect shell. On the other hand, there are extensive ranges of geometrical dimensions for which the shell is insensitive to imperfections, and, therefore it would exhibit stable post-critical behavior and have a load-carrying capacity beyond the bifurcation point. The range of imperfection sensitivity depends strongly on the material anisotropy, and also on the shell thickness and whether the end pressure loading is included or not. For example, for the circumferentially reinforced graphite/epoxy example case studied, it was found that the structure is not sensitive to imperfections for values of the Batdorf length parameter z˜ above ≃270, whereas for the axially reinforced case the structure is imperfection-sensitive even at the high range of length values; for the isotropic case, the structure is not sensitive to imperfections above z˜ ≃ 1000.