The island divertor topology of the Wendelstein 7-X (W7-X) scrape-off-layer exhibits regions of highly varying connection length. Here, we present drift-plane simulations of seeded filaments in regions of sharp transitions in parallel connection length – a parameter which dictates the propagation regime for plasma blobs. It is determined that a transition in parallel connection length alters the trajectory of filaments; filaments which enter regions of lower connection length are decelerated, and vice versa. It is also determined that if the lobes of a potential dipole created by diamagnetic drifts within the filament exist in two regions of distinct parallel connection length, the filament is then steered towards the region of higher connection length. The extreme case of a narrow region of varying connection length can also alter the trajectory of a filament, depending on the extent of this region. Finally, simulations mimicking the view from the W7-X gas puff imaging (GPI) diagnostic view plane are presented. It is determined that filaments in the view of the W7-X GPI diagnostic exhibit a predominantly poloidal propagation due to the radial electric field, since the radial velocity is relatively small.