We point out that, contrary to general belief, generic supersymmetric models are not technically unnatural in the limit of very large values of the parameter tan(beta) when radiative corrections are properly included. Rather, an upper limit on tan(beta) only arises from the requirement that Yukawa couplings remain perturbative up to some high scale. We quantify the relation between this scale and the maximum value of tan(beta). Whereas tan(beta) is limited to lie below 50-70 in the mSUGRA model, models with a much lower scale of new physics (beyond supersymmetry) may have tan(beta) < 150-200.