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Driven by the difficulty in achieving complete security with technical tools, business investigators are looking into organizational and behavioral issues that could help make systems more secure. This chapter looks at the security of systems from the organizational perspective. Specifically, this study attempts to identify if different organizations have different predisposition to particular type(s) of security threat sources. Using publicly available security breach data from a privacy rights clearinghouse to investigate which organizational characteristics predisposes an institution to an external or internal threat source, it was concluded that as size of organization and the number of its valuable documents increase by one unit, the organization's probability of suffering an internal attacks decrease. Furthermore, when executive members have a business degree rather than information-security-related degrees, the likelihood of suffering an internal attack increases. Also, the probability of an organization suffering an internal or external attack is not based on its industry type.