INTRODUCTION When an individual faces a single source of risk, the optimal insurance contract contains full insurance above a deductible when the premium only depends upon the actuarial value of the contract. This result was established not only under expected utility (Arrow 1965; Raviv 1968) but also for any non-expected utility framework that satisfies the second order stochastic dominance (SSD) property (see Machina 1995). Besides Gollier and Schlesinger (1996) have shown that the superiority of the deductible policy results from its better ability to reduce the variability of final wealth for a given cost of insurance. More specifically they prove that any insurance contract of equal cost will be dominated, in the second order sense, by one with a deductible policy. Although this result turned out to be very important in many respects, its practical relevance is limited by the assumption that there is only one source of uncertainty. In practice, people and firms face many simultaneous sources of risk and they have to decide both on the amount of their total insurance budget and on its allocation among the different sources of risk. Recently, Gollier and Schlesinger (1995) showed that people would like to cover multiple risks by purchasing an contract covering all risks at the same time, with full insurance above a deductible on the aggregate loss. Unfortunately, such an umbrella contract is rarely offered in reality. As a consequence, decision-makers have to consider the optimal level of coverage for each risk separately. In this context, Gollier and Schlesinger prove that it is optimal to purchase contracts with full insurance above a deductible for each peril. In this paper, we extend all these results by considering rules that should be followed in choosing the deductible level for each risk in terms of its characteristics. To be more specific, we consider an individual who faces two pure risks, [Mathematical Expression Omitted] and [Mathematical Expression Omitted] which differ both in terms of the of the loss occurrence ([p.sub.1] and [p.sub.2]) and in terms of the level of potential loss ([L.sub.1] and [L.sub.2], respectively).(1) For instance, [Mathematical Expression Omitted] might be a low frequency risk ([p.sub.1] low, e.g. and earthquake risk or the risk of cancer in the year to come for a young healthy individual) with a high potential loss ([L.sub.1]). On the contrary, [Mathematical Expression Omitted] may stand for a risk likely to materialize ([p.sub.2] is high) but with moderate or mild severity ([L.sub.2] is not too large). Given that insurance is offered separately for each risk, how should the optimal deductibles ([[D.sub.1].sup.*] and [[D.sub.2].sup.*]) compare to each other? Intuition suggests that one should cut down the large losses and select deductible levels so that the net loss (the loss minus the indemnity) should be equal for each risk. After all, the Arrow's deductible result suggests that it is optimal not to indemnify any loss below a limit that is the same for any source of risk affecting the wealth of the insured person. If this extension of the Arrow's result were correct, one would select equal levels of deductible for each risk. In this paper we show that such a policy is not, in general, optimal despite it's a priori intuitive appeal. Reducing the deductible has two contradictory effects on expected utility. First, it increases the premium. Second, it increases the indemnity in case of loss. It is a priori not clear how a change in the of loss affects the optimal deductible which is a best compromise between these two adverse effects. In fact, in most cases, a strong probability effect will be at work inducing the individual to choose low deductibles (hence, high coverage) for those risks that are very unlikely. Hence, our paper tends to support the sometimes held view that insurance is the most appropriate risk management tool for low frequency risks. …