This chapter addresses contemporary challenges of digital trade secret protection in the digital era, with particular attention to the legal challenges that spring from fast technological development. The study goes under way on the definition of the concept of digital trade secret and different ways in which digital trade secrets may be infringed, such as unauthorized disclosure by people who have had a certain previous relationship with an asset, as well as legal exemptions under which it might be justified to make such disclosure. It also looks at the way organizations protect their own sensitive information and the effect of new technologies on commercial data confidentiality. The chapter ends with a highlight of the critical risks that come with breaches of digital trade secrets not only to trust in business relations but also to the general economy. In light of the results, there is evidence that more violations are on the rise with the spread of digital technologies and calls for an urgent need to update the legal frameworks to cater to these sailing tides. It called for stiffer penalties against people and organizations that are caught up with illegal disclosure of digital trade secrets and, therefore, revamping the legal provisions towards the protection of these secrets in the era of digitalization.