We evaluate the orbital evolution and several plausible origins scenarios for the mutually inclined orbits of Upsilon Andromedae c and d. These two planets have orbital elements that oscillate with large amplitudes and lie close to the stability boundary. This configuration, and in particular the observed mutual inclination, demands an explanation. The planetary system may be influenced by a nearby low-mass star, Upsilon And B, which could perturb the planetary orbits, but we find it cannot modify two coplanar orbits into the observed mutual inclination of ~30 deg. However, it could incite ejections or collisions between planetary companions that subsequently raise the mutual inclination to >30 deg. Our simulated systems with large mutual inclinations tend to be further from the stability boundary than Upsilon And, but we are able to produce similar systems. We conclude that scattering is a plausible mechanism to explain the observed orbits of Upsilon And c and d, but we cannot determine whether the scattering was caused by instabilities among the planets themselves or by perturbations from Upsilon And B. We also develop a procedure to quantitatively compare numerous properties of the observed system to our numerical models. Although we only implement this procedure to Upsilon And, it may be applied to any exoplanetary system.