With present and future observations becoming of higher and higher quality, it is timely and necessary to investigate the most significant theoretical uncertainties in the predictions of inflation. We show that our ignorance of the entire history of the Universe, including the physics of reheating after inflation, translates to considerable errors in observationally relevant parameters. Using the inflationary flow formalism, we estimate that for a spectral index $n$ and tensor/scalar ratio $r$ in the region favored by current observational constraints, the theoretical errors are of order $Delta n / | n - 1| sim 0.1 - 1$ and $Delta r /r sim 0.1 - 1$. These errors represent the dominant theoretical uncertainties in the predictions of inflation, and are generically of the order of or larger than the projected uncertainties in future precision measurements of the Cosmic Microwave Background. We also show that the lowest-order classification of models into small field, large field, and hybrid breaks down when higher order corrections to the dynamics are included. Models can flow from one region to another.