How do we know the Riemann Sum gives us the area under the curve?

I'm currently learning calculus (high school senior), and I am not comfortable with the idea that the limit of the sums of rectangles actually converges to the area under the curve. I know it looks like it does, but how do we know for sure? Couldn't the tiny errors beneath/over the curve accumulate as we add more and more rectangles? What's troubling me is the whole Pi = 4 thing with the staircase approximating a circle pointwise, and how it's wrong and the perimeter of the staircase shape does not approach the circumference of the circle, even though pointwise it does approach a circle. So how are the increasingly many, increasingly small errors in Riemann sums any different? How do we know the error in each step decreases faster than the number of errors increases? I would really like to see a proof of this.

Thanks so much!

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