Bertrand's Problem is often statet in the following way: Given a circle. Find the probability that a chord chosen at random be longer than the side of an inscribed equilateral triangle (Solutions).

Since one can easily forget the whole problem or how the solutions are constructed, I was quite happy to find the following example (adapted from van Fraassen 1989) that nicely illustrates how Bertrand-stlyle paradoxes work[1]:

A factory produces cubes with side-length between 0 and 1 foot; what is the probability that a randomly chosen cube has side-length between 0 and 1/2 a foot? The tempting answer is 1/2, as we imagine a process of production that is uniformly distributed over side-length. But the question could have been given an equivalent restatement: A factory produces cubes with face-area between 0 and 1 square-feet; what is the probability that a randomly chosen cube has face-area between 0 and 1/4 square-feet? Now the tempting answer is 1/4, as we imagine a process of production that is uniformly distributed over face-area. This is already disastrous, as we cannot allow the same event to have two different probabilities (especially if this interpretation is to be admissible!). But there is worse to come, for the problem could have been restated equivalently again: A factory produces cubes with volume between 0 and 1 cubic feet; what is the probability that a randomly chosen cube has volume between 0 and 1/8 cubic-feet? Now the tempting answer is 1/8, as we imagine a process of production that is uniformly distributed over volume. And so on for all of the infinitely many equivalent reformulations of the problem (in terms of the fourth, fifth, … power of the length, and indeed in terms of every non-zero real-valued exponent of the length). What, then, is the probability of the event in question?

{The paradox arises because the principle of indifference can be used in incompatible ways. We have no evidence that favors the side-length lying in the interval [0, 1/2] over its lying in [1/2, 1], or vice versa, so the principle requires us to give probability 1/2 to each. Unfortunately, we also have no evidence that favors the face-area lying in any of the four intervals [0, 1/4], [1/4, 1/2], [1/2, 3/4], and [3/4, 1] over any of the others, so we must give probability 1/4 to each. The event ‘the side-length lies in [0, 1/2]’, receives a different probability when merely redescribed. And so it goes, for all the other reformulations of the problem. We cannot meet any pair of these constraints simultaneously, let alone all of them.}

[1] Interpretations of Probability, Stanford Encyclopedia of Philosophy