The largest part of any gravitational-wave inspiral of a compact binary can be understood as a slow, adiabatic drift between the trajectories of a certain referential conservative system. In many contexts, the phase space of this conservative system is smooth and there are no "topological transitions" in the phase space, meaning that there are no sudden qualitative changes in the character of the orbital motion during the inspiral. However, in this chapter we discuss the cases where this assumption fails and non-linear and/or non-smooth transitions come into play. In integrable conservative systems under perturbation, topological transitions suddenly appear at resonances, and we sketch how to implement the passage through such regions in an inspiral model. Even though many of the developments of this chapter apply to general inspirals, we focus on a particular scenario known as the Extreme mass ratio inspiral (EMRI). An EMRI consists of a compact stellar-mass object inspiralling into a supermassive black hole. At leading order, the referential conservative system is simply geodesic motion in the field of the supermassive black hole and the rate of the drift is given by radiation reaction. In Einstein gravity the supermassive black hole field is the Kerr space-time in which the geodesic motion is integrable. However, the equations of motion can be perturbed in various ways so that prolonged resonances and chaos appear in phase space as well as the inspiral, which we demonstrate in simple physically motivated examples.