We point out that the massive modes of closed superstring theories may play a crucial role in the last stages of black hole evaporation. If the Bekenstein-Hawking entropy describes the true degeneracy of a black hole — implying loss of quantum coherence and the unitary evolution of quantum states-it becomes entropically favorable for an evaporating black hole to make a transition to a state of massive string modes. This in turn may decay into massless modes of the string (radiation) avoiding the naked singularity exposed by black hole evaporation in the semiclassical picture. Alternatively, quantum coherence may be maintained if the entropy of an evaporating black hole is much larger than that given by the Bekenstein-Hawking formula. In that case, however, the transition to massive string modes is unlikely. String theories might thus resolve the difficulty of the naked singularity, but it appears likely that they will still involve loss of quantum coherence.