We define the observational parameter regime necessary for observing low‐altitude ionospheric origins of high‐latitude ion upflow/outflow. We present measurement challenges and identify a new analysis technique which mitigates these impediments. To probe the initiation of auroral ion upflow, it is necessary to examine the thermal ion population at 200–350 km, where typical thermal energies are tenths of eV. Interpretation of the thermal ion distribution function measurement requires removal of payload sheath and ram effects. We use a 3‐D Maxwellian model to quantify how observed ionospheric parameters such as density, temperature, and flows affect in situ measurements of the thermal ion distribution function. We define the viable acceptance window of a typical top hat electrostatic analyzer in this regime and show that the instrument's energy resolution prohibits it from directly observing the shape of the particle spectra. To extract detailed information about measured particle population, we define two intermediate parameters from the measured distribution function, then use a Maxwellian model to replicate possible measured parameters for comparison to the data. Liouville's theorem and the thin‐sheath approximation allow us to couple the measured and modeled intermediate parameters such that measurements inside the sheath provide information about plasma outside the sheath. We apply this technique to sounding rocket data to show that careful windowing of the data and Maxwellian models allows for extraction of the best choice of geophysical parameters. More widespread use of this analysis technique will help our community expand its observational database of the seed regions of ionospheric outflows.