Many engineering tasks can be formulated as dynamic optimization or open-loop optimal control problems, where we search a priori for the input profiles to a dynamic system that optimize a given performance measure over a certain time period. Further, many systems of interest in the chemical processing industries experience significant discontinuities during transients of interest in process design and operation. This paper discusses three classes of dynamic optimization problems with discontinuities: path-constrained problems, hybrid discrete/continuous problems, and mixed-integer dynamic optimization problems. In particular, progress toward a general numerical technology for the solution of large-scale discontinuous dynamic optimization problems is discussed.