People worried about privacy often think our personal data is being shared too easily. But the real issue is actually the opposite: our data doesn't flow smoothly enough, pushing companies to resort to cheaper or easier— sometimes illegal—shortcuts just to speed up data exchanges, which more often than not aren’t the most privacy-friendly options. We want to build a world where personalized, tech-assisted, digital trust enables parties to reliably and sustainably exchange data, goods, and services, negotiating on the appropriate legal ground to do so, as an alternative to today’s overuse and misuse of informed consent. To facilitate these mutually beneficial interactions, we are developing technologies to assist with legal processes towards creating and maintaining long-term trust relationships between humans, businesses and machines. In this interactive workshop, we are presenting these technologies and invite participants to actively engage in discussions that bridge theory and implementation.