$$f(x) = \begin{cases} x^2 \sin(x^{-1}), & x \neq 0 \\ 0, & x = 0 \end{cases}$$
This function is diffrentiable everywhere and continuously differentiable everywhere except 0, where the derivative has an oscillating discontinuity. It seems like if a function is differentiable on an interval containing the discontinuity in the derivative, you couldn’t get the derivative to be discontinuous any other way besides an oscillating discontinuity because then it just wouldn’t exist. Is that true?
For example, if you tried to make the derivative a step function, the function would be piecewise linear and not differentiable when the slope changes.