This chapter starts with the widely accepted idea that one of the key principles of the rule of law is equality before the law. We draw on socio-legal research to demonstrate how already disadvantaged citizens are commonly disproportionately affected by the application of apparently neutral rules. We then draw on our own research into two rather different enforcement regimes—against landlords, on the one hand, and company directors, on the other—to demonstrate how the enforcement of such laws can become skewed according to wealth and power. These are traditional socio-legal issues to which the company director scheme adds by demonstrating that, even around algorithmic regulation, discretionary spaces open up.