What sort of legal and policy choices would lead to more secure and safer software and computing-enabled devices? The patchwork of existing legal regimes in the US is based on regulations imposed on a few verticals (finance, healthcare, and education in particular), and a complex web of compliance frameworks, contractual provisions, and consumer lawsuits. As we think about making software safer and more secure for users, the policy choices we preference now may have long reaching effects. This talk will explore the implications of relying on software liability or other ex-post options vs. regulations or similar ex-ante choices.