Suppose $f:[a,b]\to\mathbb{R}$ is strictly increasing and left-continuous. Does it follow that $f$ maps Borel subsets of $[a,b]$ to Lebesgue measurable subsets of $\mathbb{R}$?
My intuition tells me that this is the case because the fact that $f$ is non-decreasing on a closed interval $[a,b]$ implies that $f$ has at most countably many discontinuities. But I cannot continue from there.
Yes, it does.
Let me just sketch the proof. First, show that $f([a,b])$ equals $[f(a), f(b)]$ with a countable number of half-open intervals removed (corresponding to the jumps of $f$). In particular, $f([a,b])$ is Borel.
Next, show that for any interval $[c,d] \subset [a,b]$, we have $f([c,d]) = [f(c), f(d)] \cap f([a,b])$ which is also Borel.
Now let $\mathcal{F}$ be the collection of all sets $A \subset [a,b]$ such that $f(A)$ is Borel. We have just shown $\mathcal{F}$ contains all the closed intervals. Since $f\left(\bigcup_n A_n\right) = \bigcup_n f(A_n)$, $\mathcal{F}$ is closed under countable unions. And since $f$ is injective, we have $f(A^c) = f([a,b]) \setminus f(A)$ so that $\mathcal{F}$ is closed under complements. Thus $\mathcal{F}$ is a $\sigma$-algebra and it contains all the Borel subsets of $[a,b]$.