We present a homotopic approach to solving challenging, optimization-based motion planning problems. The approach uses Homotopy Optimization, which, unlike standard continuation methods for solving homotopy problems, solves a sequence of constrained optimization problems rather than a sequence of nonlinear systems of equations. The insight behind our proposed algorithm is formulating the discovery of this sequence of optimization problems as a search problem in a multidimensional homotopy parameter space. Our proposed algorithm, the Probabilistic Homotopy Optimization algorithm, switches between solve and sample phases, using solutions to easy problems as initial guesses to more challenging problems. We analyze how our algorithm performs in the presence of common challenges to homotopy methods, such as bifurcation, folding, and disconnectedness of the homotopy solution manifold. Finally, we demonstrate its utility via a case study on two dynamic motion planning problems: the cart-pole and the MIT Humanoid.

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