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The recent wave of teacher strikes across the U.S. presented an important opportunity for activist teachers to expand their anti-privatization movement by tethering this movement to teacher demands around work related issues like better funding and higher wages. In Oakland, teachers who had been organizing against privatization for years laid the groundwork to be able to capitalize on their strike in this way. This article examines how Oakland’s activist teachers worked towards this moment, how they reflected on their efforts, and how they thought about shifting their organizing in response to their reflections from the strike. I show how activist teachers in Oakland made strategic decisions as social movement entrepreneurs (Johnston & Noakes, 2005) through their praxis (Freire, 2018).