I've seen the equation:
$$ E[X\mathbb{I}_{\{Y\leq y\}}] = E[X|Y\leq y]P(Y\leq y) \Leftrightarrow \frac{E[X\mathbb{I}_{\{Y\leq y\}}]}{P(Y\leq y)} = E[X|Y\leq y]$$
but never found a proof (I'm sure there is one), so here is my attempt:
$$ E[X|Y\leq y] := \int x f_{X|Y}(x|y) dx $$
\begin{align*} E[X\mathbb{I}_{\{Y\leq y\}}] &= \int_\mathcal{S_X} \int_\mathcal{S_Y} x\mathbb{I}_{\{Y\leq y\}}f_{X, Y}(x,y) dxdy \\ &= \int_\mathcal{S_X} \int_\mathcal{S_Y}x\mathbb{I}_{\{Y\leq y\}}f_{X|Y}(x|y)f_Y(y) dxdy \\ &= \int_\mathcal{S_X} \bigg(\int_\mathcal{S_Y} \mathbb{I}_{\{Y\leq y\}}f_Y(y)dy\bigg)xf_{X|Y}(x|y) dx \\ &= P(Y\leq y) \int_\mathcal{S_X} xf_{X|Y}(x|y) dx \\ &= P(Y\leq y) E[X|Y\leq y] \\ \end{align*}
Is my argument correct?
Let me give you an effort to justify what I asserted in a comment to your question:
Let's start with a probability space $(\Omega,\mathcal A,P)$ and let $A$ be an event with $P(A)>0$. If $X$ is some integrable rv defined on the space then its expectation is of course determined by $P$.
Now let us define a new probability measure $P(\cdot|A)$ on the space by:$$P(B|A):=\frac{P(B\cap A)}{P(A)}$$or equivalently:$$P(B|A)P(A)=P(B\cap A)$$ It is straightforward to prove (it is only here where we can use that word properly) that the integral of $X$ wrt this probability measure equals:$$\frac{\mathbb EX1_A}{P(A)}$$ Denoting this integral as $\mathbb E[X|A]$ we arrive at:$$\mathbb E[X|A]P(A)=\mathbb EX1_A$$