This is a followup to this previous question: Do homomorphisms $H \to \operatorname{Aut}(K)$ that coincide at the level of $\operatorname{Out}(K)$ induce isomorphic semidirect products?
I am trying to understand why $S_n$ doesn't seem to appear as a normal subgroup of a nontrivial semidirect product except when $n=6$. Two relevant facts: $S_n$ is centerless when $n \geq 3$, and its outer automorphism group is trivial except when $n = 6$. This raises the more general question:
If $\phi,\psi:H \to \operatorname{Aut}(K)$ induce the same map $H \to \operatorname{Out}(K)$, and if $K$ is centerless, then is it true that $K \rtimes_\phi H \cong K \rtimes_\psi H$?