Chances are that we are using the definition of R-S integral as found in Rudin's Principle of Mathematical Analysis. That is, the upper R-S sum is $U(P,f,\alpha)=\sum_{i=1}^nM_i (\alpha(x_i)-\alpha(x_{i-1}))$ where $M_i=\sup\{f(x): x\in [x_{i-1},x_i]\}$. The upper integral is the infimum of all upper sums. The lower integral is defined similarly, and when both are equal, we declare the function integrable wrt $\alpha$.
Confession: I hate the above definition. It leads to ridiculous hair-splitting: the functions $\alpha_1(t)=\begin{cases} 1,\qquad t>0 \\ 0,\qquad t\le 0\end{cases}$ $\alpha_2(t)=\begin{cases} 1,\qquad t\ge 0 \\ 0,\qquad t< 0\end{cases}$ $\alpha_3(t)=\frac{1}{2}(\alpha_1+\alpha_2)$ are all different ways to assign unit mass to the point at $0$. The first puts all mass on the "right half of the point", the second puts it all on the "left half", and the third gives $1/2$ to each half of the point.
So, a function $g$ is integrable with respect to $\alpha_1$ iff $g(0)=g(0+)$ - it does not have to be continuous from the left at $0$. Similarly, it is integrable wrt $\alpha_2$ iff $g(0)=g(0-)$. In both of these examples the set of discontinuities may well be all of $\mathbb R$, yet we have integrability as long as one-sided continuity at $0$ holds. Thus, integrability cannot be expressed in terms of the set of discontinuity $D$: you have to look at the set of right discontinuities $D_+$ and left discontinuities $D_-$. And it's not about measure in the usual sense, because we are "measuring" half-points.
Honestly, I don't know why people do this to themselves instead of assuming one-sided continuity of $\alpha$ and defining $M_i$ in terms of half-open intervals.