A comprehensive theoretical analysis of end-fire coupling between dielectric-loaded surface plasmon polariton and rib/wire silicon-on-insulator (SOI) waveguides is presented. Simulations are based on the 3-D vector finite element method. The geometrical parameters of the interface are varied in order to identify the ones leading to optimum performance, i.e., maximum coupling efficiency. Fabrication tolerances about the optimum parameter values are also assessed. In addition, the effect of a longitudinal metallic stripe gap on coupling efficiency is quantified, since such gaps have been observed in fabricated structures. Finally, theoretical results are compared against insertion loss measurements, carried out for two distinct sets of samples comprising rib and wire SOI waveguides, respectively.