We study problems concerning the Samuel compactification of the automorphism group of a countable first-order structure. A key motivating question is a problem of Furstenberg and a counter-conjecture by Pestov regarding the difference between $S\left(G\right)$, the Samuel compactification, and $E\left(M\right(G\left)\right)$, the enveloping semigroup of the universal minimal flow. We resolve Furstenberg’s problem for several automorphism groups and give a detailed study in the case of $G=S_{\infty }$, leading us to define and investigate several new types...