We study dynamic measure transport for generative modelling in the setting of a stochastic process $X_\bullet$ whose marginals interpolate between a source distribution $P_0$ and a target distribution $P_1$ while remaining independent, i.e., when $(X_0,X_1)\sim P_0\otimes P_1$. Conditional expectations of this process $X_\bullet$ define an ODE whose flow map transports from $P_0$ to $P_1$. We discuss when such a process induces a \emph{straight-line flow}, namely one whose pointwise acceleration vanishes and is therefore exactly integrable by any first-order method. We first develop multiple characterizations of straightness in terms of PDEs involving the conditional statistics of the process. Then, we prove that straightness under endpoint independence exhibits a sharp dichotomy. On one hand, we construct explicit, computable straight-line processes for arbitrary Gaussian endpoints. On the other hand, we show straight-line processes do not exist for targets with sufficiently well-separated modes. We demonstrate this through a sequence of increasingly general impossibility theorems that uncover a fundamental relationship between the sample-path behavior of a process with independent endpoints and the space-time geometry of this process' flow map. Taken together, these results provide a structural theory of when straight generative flows can, and cannot, exist.

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