Perhaps, the most insightful analysis (possibly to this day) of indeterminism in classical mechanics and its implications was given by Joseph Boussinesq, best known for his work on solitons, in a book long essay Reconciliation of Mechanical Determinism with Moral Freedom (1878). His ideas were based on the general theory of solutions to differential equations that was undergoing systematization at the time. In particular, solutions were classified into regular, which depend on initial data continuously, and singular, e.g. unstable equilibria (like the circular pendulum in the upright position), where infinitesimal deviations produce large changes in the outcome. Boussinesq further distinguished between asymptotic and singular solutions proper, like equilibrium at the top of Norton dome, which can be reached in finite time, and produces non-uniqueness of solutions under time reversal. In fact he used an example almost identical to the Norton dome according to Popular Science Monthly (1882):"It then reaches the apex with a velocity of zero, and remains there till it pleases some directingguiding principle residing there to give it an impulse in a required direction, which, although it is equal to nothing, shall yet be competent to let it glide down the paraboloid again".
Boussinesq saw these singular "bifurcations" (his word) as creating gaps in causal chains, and suggesting an additional "directing"guiding principle" operating in living organisms. This answered the objection, raised earlier by Helmholtz, Du Bois-Reymond and others against such a principle, that conservation of energy precludes its operation. Maxwell praised the idea in a letter to Galton (1879):"it may at any instant, at its own sweet will, without exerting any force or spending any energy, go off along that one of the particular paths which happens to coincide with the actual condition of the system at that instant. In most of the former methods... there was a certain small but finite amount of... trigger-work for the Will to do. Boussinesq has managed to reduce this to mathematical zero... I think Boussinesq’s method is a very powerful one against metaphysical arguments about cause and effect and much better than the insinuation that there is something loose about the laws of nature..."
It was against this backdrop that Boussinesq advanced his idea. Earlier free will issues were in the domain of philosophers, who largely assumed, along with the common public, that mechanical laws did not apply to the mental. Bertrand, in his 1878 critique of Boussinesq gave a mathematician's version of this position (which incidentally rejects Laplace's extrapolation): "the results of equations could not attain absolute precision”, and “the certainty of equations cannot be greater than the certainty of principles from which they stem”, so it is naive to expect that solutions will be "loyally followed" even along regular segments. Bertrand's criticism was off the mark, Boussinesq did not suggest that mechanical description was precise, he explicitly described bifurcations as only structural toy models for what might be happening in the living organisms, but toy models with the benefit of mathematical precision. In 1880 Du Bois-Reymond acknowledged Boussinesq, and his precursors Saint-Venant and Cournot, but deemed their position unsatisfactory. Soon attention turned to new physics, and Boussinesq's programme of exploring the nature of "directing"guiding principle" scientifically fell into oblivion until recent times. Although some of his ideas about the role of causal gaps and directingthe guiding principle in the mind-body problem were re-explored since 1950s by Heisenberg and Wigner (later Penrose and others) with quantum mechanics in place of classical.