When does randomization speed up algorithms and it "shouldn't"?
I don’t know whether randomization “should” or “shouldn’t” help, however, integer primality testing can be done in time $\tilde O(n^2)$ using randomized Miller–Rabin, while as far as I know, the best known deterministic algorithms are $\tilde O(n^4)$ assuming GRH (deterministic Miller–Rabin) or $\tilde O(n^6)$ unconditionally (variants of AKS).