Let $Omega$ be the complement of a connected, essential hyperplane arrangement. We prove that every dominant endomorphism of $Omega$ extends to an endomorphism of the tropical compactification $X$ of $Omega$ associated to the Bergman fan structure on the tropicalization of $Omega$. This generalizes a previous result by Remy, Thuillier and the second author which states that every automorphism of Drinfelds half-space over a finite field $mathbb{F}_q$ extends to an automorphism of the successive blow-up of projective space at all $mathbb{F}_q$-rational linear subspaces. This successive blow-up is in fact the minimal wonderful compactification by de Concini and Procesi, which coincides with $X$ by results of Feichtner and Sturmfels. Whereas the previous proof is based on Berkovich analytic geometry over the trivially valued finite ground field, the generalization discussed in the present paper relies on matroids and tropical geometry.