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Protecting against cyber-threats is vital for every organization and can be done by investing in cybersecurity controls and purchasing cyber insurance. However, these are interlinked since insurance premiums could be reduced by investing more in cybersecurity controls. The expected utility theory and the prospect theory are two alternative theories explaining decision-making under risk and uncertainty, which can inform strategies for optimizing resource allocation. While the former is considered a rational approach, research has shown that most people make decisions consistent with the latter, including on insurance uptakes. We compare and contrast these two approaches to provide important insights into how the two approaches could lead to different optimal allocations resulting in differing risk exposure as well as financial costs. We introduce the concept of a risk curve and show that identifying the nature of the risk curve is a key step in deriving the optimal resource allocation.