After thirty years of FOSS advocacy, issue and problems in approach have begun to emerge. Strategic mistakes in approach to new technologies has often led to large areas of software endeavor to remain proprietary. While for-profit companies have been rewarded with great efficiency benefits and other perks from their adoption of FOSS, rarely do these benefits trickle down to consumers and end-users in their daily computing lives. This talk examines our past mistakes in advocacy and activism, and considers what to do next. Since its advent in the late 1980s, the Free and Open Source Software (FOSS) community now has more than thirty years of experience in strategies for advocacy and encouraging adoption of FOSS. Results have, unfortunately, been mixed. While corporate adoption by for-profit companies has led to a boon and integration of FOSS into most corporate practices, the true promise of software rights and freedoms — the ability of individual hobbyist and consumers to participate on equal footing with the largest software producers in the world — mostly eludes our community. This talk examines the wins, losses and challenges that FOSS advocacy has faced in the last thirty years. We'll explore how failures to foresee both web application deployment and the advent of advertising-based app-oriented software deployment led to serious strategic errors in advocacy and focus of attention. Many of these problems remain difficult to address, and only frank discussion among activists will reveal new approaches to continue a vibrant FOSS community into the next generation.