The imposition of duties will only result in practical differences on the ground if regulated parties comply with their obligations. For this reason monitoring and enforcement are said to be essential components in the effective operation of any regulatory system.. The question of how to motivate parties to comply with their legal duties has generated a considerable body of scholarship, which will be touched on in this chapter. Regulatory enforcement is more complex where legal frameworks with competing objectives overlap. For example, the operation of laws is complicated where there is an overlap between laws which prohibit digital discrimination and promote access to information, and those which seek to restrict the use of information. This chapter will illustrate that the enforcement of anti-discrimination laws and laws which promote equality are generally weak. In contrast, copyright laws are robustly enforced with substantial sanctions for non-compliance. The interaction between these competing regimes arguably sends the message that protecting rights-holders’ interests in controlling use of information is a higher priority than complying with anti-discrimination laws and laws which promote equal access to information.