Best I can tell is that overflow is undefined behavior for signed ints in C/C++ so -O3 with gcc might remove a check that could only be true if UB occurred.
The compound predicate in my example above coupled with the fact that the compiler doesn’t reason about the precondition in the prior assert (y is non-negative) means this specific example wouldn’t be optimized away, but bluGill does have a point.
An example of an assert that might be optimized away:
int addFive(int x) {
int y = x + 5;
assert(y >= x);
return y;
}