Abstract. Growth in electronic commerce has enabled businesses to reduce costs and expand markets by deploying information technology through new and existing business practices. However, government laws and regulations require businesses to employ reasonable security measures to thwart risks associated with this technology. Because many security vulnerabilities are only discovered after attacker exploitation, regulators update their interpretation of reasonable security to stay current with emerging threats. With a focus on determining what businesses must do to comply with these changing interpretations of the law, we conducted an empirical, multi-case study to discover and measure the meaning and evolution of "reasonable" security by examining 19 regulatory enforcement actions by the U.S. Federal Trade Commission (FTC) over a 10 year period. The results reveal trends in FTC enforcement actions that are institutionalizing security knowledge as evidenced by 39 security requirements that mitigate 110 legal security vulnerabilities.