Azobenzenes are candidates for efficient, photochemically triggered switching in devices of molecular size. The cis-azobenzene isomer is inherently chiral because of its helicity. Applying OM2/MRCI surface-hopping molecular dynamics simulations, we analyze chiral photoisomerization pathways in cis-azobenzene and correlate oscillatory features in the population decay to modes that trigger motion toward and from the S₁/S₀ crossing region.