The real-time propagator of the symmetric Rosen-Morse, also known as the symmetric modified P\"oschl-Teller, barrier is expressed in the Picard-Lefschetz path integral formalism using real and complex classical paths. We explain how the interference pattern in the real-time propagator and energy propagator is organized by caustics and Stoke's phenomena, and list the relevant real and complex classical paths as a function of the initial and final position. We discover the occurrence of singularity crossings, where the analytic continuation of the complex classical path no longer satisfies the boundary value problem and needs to be analytically continued. Moreover, we demonstrate how these singularity crossings play a central role in the real-time description of quantum tunneling.