This study presents results from magnetic field line conjunctions between the medium-Earth orbiting Demonstration and Science Experiments (DSX) satellite and the low-Earth orbiting VLF Propagation Mapper (VPM) satellite. DSX transmitted at very low frequencies (VLF) towards VPM, which was equipped with a single-axis dipole electric field antenna, when the two spacecraft passed near the same magnetic field line. VPM did not observe DSX signals in any of the 27 attempted conjunction experiments; the goal of this study, therefore, is to explain why DSX signals were not received. Explanations include i) the predicted power at LEO from DSX transmissions was too low for VPM to observe; ii) VPM’s trajectory missed the “spot” of highest intensity due to the focused ray paths reaching LEO; or iii) rays mirrored before reaching VPM. Different combinations of these explanations are found. We present ray-tracing analysis for each conjunction event to predict the distribution of power and wave normal angles in the vicinity of VPM at LEO altitudes. We find that, for low-frequency (below 4kHz) transmissions, nearly all rays mirror before reaching LEO, resulting in low amplitudes at LEO. For mid- and high-frequency transmissions (~8kHz and 28kHz respectively), the power at LEO is above the noise threshold of the VPM receiver (between 0.5µV/m and 1µV/m). We conclude that the antenna efficiency and plasmasphere model are critical in determining the predicted power at LEO, and are also the two most significant sources of uncertainty that could explain the apparent discrepancy between predicted amplitudes and VPM observations.