There is empirical evidence from a range of disciplines that as the connectivity of a network increases, we observe an increase in the average fitness of the system. But at the same time, there is an increase in the proportion of failure/extinction events which are extremely large. The probability of observing an extreme event remains very low, but it is markedly higher than in the system with lower degrees of connectivity. We are therefore concerned with systems whose properties are not static but which evolve dynamically over time. The focus in this paper, motivated by the empirical examples, is on networks in which the robustness or fragility of the vertices is not given, but which themselves evolve over time We give examples from complex systems such as outages in the US power grid, the robustness properties of cell biology networks, and trade links and the propagation of both currency crises and disease. We consider systems which are populated by agents which are heterogeneous in terms of their fitness for survival. The agents are connected on a network, which evolves over time. In each period agents take self-interested decisions to increase their fitness for survival to form alliances which increase the connectivity of the network. The network is subjected to external negative shocks both with respect to the size of the shock and the spatial impact of the shock. We examine the size/frequency distribution of extinctions and how this distribution evolves as the connectivity of the network grows. The results are robust with respect to the choice of statistical distribution of the shocks. The model is deliberately kept as parsimonious and simple as possible, and refrains from incorporating features such as increasing returns and externalities arising from preferential attachment which might bias the model in the direction of having the empirically observed features of many real world networks. The model still generates results consistent with the empirical evidence: increasing the number of connections causes an increase in the average fitness of agents, yet at the same time makes the system as whole more vulnerable to catastrophic failure/extinction events on an near-global scale.