The Enhanced Polar Outflow Probe (e-POP) payload will be launched on a small satellite in 2007 for exploring plasma and atmospheric outflow process in the polar region. The subject of this paper is whether one can determine the properties of large-scale ionospheric structures by studying the perturbations that they cause on HF radio waves received at the e-POP satellite from ground-based transmitters such as the Canadian Advanced Digital Ionosonde (CADI). The perturbations on the received waves have been investigated using numerical ray-tracing methods. These simulation results show that ionospheric irregular structures lead to a complex pattern of amplitude, propagation time delay, Doppler frequency, and direction-of-arrival (DOA) effects on the HF radio waves received at the satellite. The simulations also show that ionospheric density structure cannot be measured unambiguously using a single wave property. Therefore a “catalog” of HF signatures of typical ionospheric irregularities has been established in order to be able to interpret the e-POP HF measurements in terms of ionospheric structures.