Cyber-security has recently become a topic of interest in behavioral economics, following nascent awareness on the role of human-related factors in the genesis of cyber-risk. Here, we propose four studies to address what we believe are the most critical questions in information security: (i) how to improve resilience towards cyber-threats at organizational level in the face of a fast moving target? (ii) how does the cost of cyber-security impact society as a whole when the industry has only poor incentives to invest in information security? (iii) how can we measure unobservable factors pertaining to human behavior in decision-making contexts under uncertainty? (iv) what represents the next step in behavioral information security research? To answer these questions, we identify two paradoxes as major constraints to fully-informed decision-making in the cyber-space and lay down the foundations of a more resilient approach to cyber-risk management in Chapter 1. In Chapter 2, we study how the failure to internalize the full cost of cyber-security impacts the evolution of social welfare over time. In Chapter 3, we show how to estimate a set of behavioral preference parameters based on a novel experimental setting. Finally, in Chapter 4, we describe the methodological basis of functional magnetic resonance imaging (fMRI) and discuss how this method can be used to study the neural correlates of decision-making in behavioral research. We conclude on the necessity of a more comprehensive understanding of human behavior for the design of more informed decisions in cyber-security.