We developed state-dependent life-history theory to explain the variance in clutch size decisions made by insect herbivores under a variety of ecological scenarios. An important aspect of our theory is explicit representation of the distribution of host quality and frequency of occurrence. Examination of the theory suggests that clutch size decisions can be highly non-linear with respect to host quality and variability. We then use our theory to explore the potential for bet-hedging strategies to evolve as a function of unpredictable catastrophic events that decimate entire clutches. Our analysis suggests that the benefits to employing such a strategy will frequently be outweighed by costs brought on by delayed oviposition.