Let $E$ be an infinite-dimensional complex Hilbert space and $\mathcal{L}(E)$ be the algebra of all bounded linear operators from $E$ to $E$.
Let $M$ be a subspace of $E$ and $T\in \mathcal{L}(E)$. It is true that $$T(M^\perp)\subseteq M^\perp \Longleftrightarrow T^*(M)\subseteq M?$$
\begin{gather*}T(M^{\perp})\subset M^{\perp}\iff \left(x\in M^{\perp}\Rightarrow Tx\in M^{\perp}\right) \iff \\ \iff \left[x\in M^{\perp} \Rightarrow \left\langle Tx,y\right\rangle=0\;\forall y\in M\right]\iff \left[x\in M^{\perp} \Rightarrow \left\langle x,T^*y\right\rangle=0\;\forall y\in M\right]\iff \\ \iff T^*(M)\subset (M^{\perp})^{\perp} \end{gather*} Now, if $M$ is closed, $(M^{\perp})^{\perp}=M$, and we are done. Otherwise, $(M^{\perp})^{\perp}=\bar{M}\neq M$, so the equivalence does not hold in general.