This paper introduces a novel generative framework for synthesising forward-looking, càdlàg stochastic trajectories that are sequentially consistent with time-evolving path-law proxies, thereby incorporating anticipated structural breaks, regime shifts, and non-autonomous dynamics. By framing path synthesis as a sequential matching problem on restricted Skorokhod manifolds, we develop the \textit{Anticipatory Neural Jump-Diffusion} (ANJD) flow, a generative mechanism that effectively inverts the time-extended Marcus-sense signature. Central to this approach is the Anticipatory Variance-Normalised Signature Geometry (AVNSG), a time-evolving precision operator that performs dynamic spectral whitening on the signature manifold to ensure contractivity during volatile regime shifts and discrete aleatoric shocks. We provide a rigorous theoretical analysis demonstrating that the joint generative flow constitutes an infinitesimal steepest descent direction for the Maximum Mean Discrepancy functional relative to a moving target proxy. Furthermore, we establish statistical generalisation bounds within the restricted path-space and analyse the Rademacher complexity of the whitened signature functionals to characterise the expressive power of the model under heavy-tailed innovations. The framework is implemented via a scalable numerical scheme involving Nyström-compressed score-matching and an anticipatory hybrid Euler-Maruyama-Marcus integration scheme. Our results demonstrate that the proposed method captures the non-commutative moments and high-order stochastic texture of complex, discontinuous path-laws with high computational efficiency.