We consider the problem of risk diversification of $\alpha$-stable heavy tailed risks. We study the behaviour of the aggregated Value-at-Risk, with particular reference to the impact of different tail dependence structures on the limits to diversification. We confirm the large evidence of sub-additivity violations, particularly for risks with low tail index values and positive dependence. So, reinsurance strategies are not allowed to exploit diversification gains, or only a very limited amount of them. Concerning the impact of tail dependence, we find the peculiar results that for high tail dependence levels the limits to diversification are uniformly lower for all the levels of dependence, and for all levels of $\alpha<2$. The result is confirmed as we move towards extreme points in the tail: in this case, we show that at some point in the tail the aggregated VaR becomes additive above some level of dependence, but this critical dependence level is lower for copulas with lower tail dependence.