In the cloud-based society, where the vast majority of social, economic and personal interactions is mediated by information communication technology (ICT), technology is no longer simply a subject of regulation but is becoming an integral part of the regulatory process. Techno-regulation, the “intentional influencing of individuals’ behavior by building norms into technological devices,” is inspiring new ways to support legal safeguards through hardware and software tools, technical solutions allowing the creation of legal relations, hampering breaches of law and even promoting norm compliance. This paper touches on these issues by focusing on Digital Labor Platforms, one of the most relevant phenomena in the gig economy. We present a research project exploring innovative techno-regulatory solutions to protect gig economy workers. The idea is to integrate, in the same strategy, legal principles, regulatory objectives and software solutions. Our attention focuses on two results of our activity—a techno-regulatory model relying on reputational mechanisms to affect the behavior of digital labor market operators and GigAdvisor, a cross-platform experimental application implementing the model.