Suppose I have a smooth Riemannian manifold $X$ with induced distance function $d$, and a bi-Lipschitz (with respect to $d$) homeomorphism $$\phi: X \to X.$$
Under what circumstances could $\phi$ be smoothable to a diffeomorphism? By "smoothable" in this case I mean "homotopic to a diffeomorphism through bi-Lipschitz homeomorphisms" (this might not be standard, I suppose). Are there any clear obstructions?