For the first time, direct comparisons of the equatorial ion pressure and pitch angle anisotropy observed by TWINS and simulated by CIMI are presented. The TWINS ENA images are from a 4-day period, 7–10 September 2015. The simulations use both the empirical Weimer 2K and the self-consistent RCM electric potentials. There are two moderate storms in succession during this period. In most cases, we find that the general features of the ring current in the inner magnetosphere obtained from the observations and the simulations are similar. Nevertheless, we do see consistent indications of enhanced electric and magnetic shielding in the TWINS observations. The simulated pressure peaks are often inside the observed peaks and more toward dusk than the measured values. There are also cases in which the measured equatorial ion pressure shows multiple peaks that are not seen in the simulations. This occurs during a period of intense AE index, suggesting time and spatially dependent injections from the plasma sheet that are not included in these simulations. The simulations consistently show regions of parallel anisotropy spanning the night side between approximately 6 and 8 RE whereas the parallel anisotropy is seen in the observations only during the main phase of the first storm. This may indicate stronger electric and magnetic shielding than is present in the simulations. The evidence form the unique global view provided by the TWIN observations strongly suggests that there are features in the ring current pressure distributions that can be best explained by enhanced electric and magnetic shielding and/or spatially-localized, short-duration injections.