Mathematical models involving switches -in the form of differential equations with discontinuities -can accomodate real-world non-idealities through perturbations by hysteresis, time-delay, discretization, and noise. These are used to model the processes associated with switching in electronic control, mechanical contact, predator-prey preferences, and genetic or cellular regulation. The effect of such perturbations on rapid switching dynamics about a single switch are somewhat benign: in the limit that the size of the perturbation goes to zero the dynamics is given by Filippov's sliding solution. When multiple switches are involved, however, perturbations can have complicated effects, as shown in this paper. In the zero-perturbation limit, hysteresis, time-delay, and discretization cause erratic variation or 'jitter' for stable sliding motion, whilst noise generates a relatively regular sliding solution similar to the canopy solution (an extension of Filippov's solution to multiple switches). We illustrate the results with a model of a switched power circuit, and showcase a variety of complex phenomena that perturbations can generate, including chaotic dynamics, exit selection, and coexisting sliding solutions.