We investigate flux vacua on a variety of one-parameter Calabi-Yau compactifications, and find many examples that are connected through continuous monodromy transformations. For these, we undertake a detailed analysis of the tunneling dynamics and find that tunneling trajectories typically graze the conifold point---particular 3-cycles are forced to contract during such vacuum transitions. Physically, these transitions arise from the competing effects of minimizing the energy for brane nucleation (facilitating a change in flux), versus the energy cost associated with dynamical changes in the periods of certain Calabi-Yau 3-cycles. We find that tunneling only occurs when warping due to back-reaction from the flux through the shrinking cycle is properly taken into account.