Many superconducting qubit systems use the dispersive interaction between the qubit and a coupled harmonic resonator to perform quantum state measurement. Previous works have found that such measurements can induce state transitions in the qubit if the number of photons in the resonator is too high. We investigate these transitions and find that they can push the qubit out of the two-level subspace. Furthermore, these transitions show resonant behavior as a function of photon number. We develop a theory for these observations based on level crossings within the Jaynes-Cummings ladder, with transitions mediated by terms in the Hamiltonian which are typically ignored by the rotating wave approximation. We confirm the theory by measuring the photon occupation of the resonator when transitions occur while varying the detuning between the qubit and resonator.