Throughout I will use the language of Orlicz norms associated with the family of functions $\psi_a(x) = \exp(x^a)-1$ for $a\in[1,\infty)$, and
$$\psi_\infty(x) = \begin{cases}\infty & x>1\\1 & x = 1\\ 0 & x < 1 \end{cases}.$$
Let $X$ be mean-zero with sub-Gaussian norm $\lVert X\rVert_{\psi_2}<\infty$. Let $Y$ be bounded in $[-B,B]$ for $B>0$. It is straightforward to show that for $X, Y$ independent, one has the bound
$$\lVert XY\rVert_{\psi_2} \leq \lVert X\rVert_{\psi_2}\lVert Y\rVert_{\psi_\infty} = B\lVert X\rVert_{\psi_2}$$
I am curious if this can be improved if one has further knowledge that $Y$ is concentrated. In particular, I know that
$$\Pr[|Y| > t\sqrt{B}] \leq \exp(-t^2),$$
e.g. something along the lines that $\lVert Y\rVert_{\psi_2} \leq \sqrt{B}$. Can one use this to show that $\lVert XY\rVert_{\psi_2} = o(B)\lVert X\rVert_{\psi_2}?$ Note that one can easily show $\lVert XY\rVert_{\psi_1} \leq \lVert X\rVert_{\psi_2}\lVert Y\rVert_{\psi_2}$, but I want a bound on the $\psi_2$ norm of the product, so this is not good enough.
I had initially thought that I could use that one definition of $\lVert XY\rVert_{\psi_2}$ is that
$$\forall \lambda>0 : \mathbb{E}[\exp(\lambda XY)] \leq \exp(\lambda^2 \lVert XY\rVert_{\psi_2}^2).$$
Conditioning on the event $|Y|>t\sqrt{B}$ is large reduces to finding an exponential upper bound on
$$\exp(\lambda^2 t^2B\lVert X\rVert_{\psi_2}^2)](1-\exp(-t^2)) + \exp(\lambda^2 B^2\lVert X\rVert_{\psi_2}^2)\exp(-t^2),$$
and perhaps by choosing $t$ appropriately one could remove the impact of this problematic second term. This argument has not worked yet, and I do not know if it is because the idea is fundamentally flawed, or the particular argument is wrong.