The Chandra X-ray Observatory (CXO) was launched on July 23, 1999 and reached its final orbit on August 7, 1999. The CXO is in a highly elliptical orbit, approximately 140,000 km X 10,000 km, and has a period of approximately 63.5 hours (approximately equals 2.65 days). It transits the Earth's Van Allen belts once per orbit during which no science observations can be performed due to the high radiation environment. The Chandra X-ray Observatory Center currently uses the National Space Science Data Center's `near Earth' AP-8/AE-8 radiation belt model to predict the start and end times of passage through the radiation belts. However, our scheduling software uses only a simple dipole model of the Earth's magnetic field. The resulting B, L magnetic coordinates, do not always give sufficiently accurate predictions of the start and end times of transit of the Van Allen belts. We show this by comparing to the data from Chandra's on-board radiation monitor, the EPHIN (Electron, Proton, Helium Instrument particle detector) instrument. We present evidence that demonstrates this mis-timing of the outer electron radiation belt as well as data that also demonstrate the significant variability of one radiation belt transit to the next as experienced by the CXO. We also present an explanation for why the dipole implementation of the AP-8/AE-8 model is not ideally suited for the CXO. Lastly, we provide a brief discussion of our on-going efforts to identify a model that accounts for radiation belt variability, geometry, and one that can be used for observation scheduling purposes.