In order to determine the origin of discontinuities which arise when the semiclassical propagator is employed to describe an infinitely long and infinitesimally thin solenoid carrying magnetic flux, we give a systematic derivation of the semiclassical limit of the motion of an otherwise free charged particle. Our limit establishes the connection of the quantum mechanical canonical angular momentum to its classical counterpart. Moreover, we show how a picture of Aharonov-Bohm interference of two half-waves acquiring Diracs magnetic phase when passing on either side of the solenoid emerges from the quantum propagator, and that the typical scale of the resulting interference pattern is fully determined by the ratio of the angular part of Hamiltons principal function to Plancks constant. The semiclassical propagator is recovered in the limit when this ratio diverges. We discuss the relation of our results to the whirling-wave representation of the exact propagator.