I am thinking about the following statement and can't seem to be able to either prove it of disprove it:
Let $G$ be a finitely generated (or even finitely presented) group, let $H < G$ be a subgroup and consider any automorphism $\varphi \in{\rm Aut}(G)$. Then it is impossible that $\varphi(H) \subsetneq H$.
I know this can easily happen if $G$ is not finitely generated.
It is possible. Take $H$ to be a free $2$-generated subgroup of a free group $F$ and $L$ be a free $2$-generated proper subgroup of $H$. Let $G$ be the HNN extension of $F$ with associated subgroups $H, L$. Then $H, L$ are conjugate in $G$. So there exists an inner automorphism of $G$ which takes $H$ to $L$. If $F$ is finitely generated, then $G$ is always finitely presented.