This presentation analyzes Lin-Manuel Miranda’s strategies for mobilizing activism on Twitter by comparing his response to hurricane recovery efforts with that of protests in Puerto Rico. I begin the presentation by outlining the rhetorical strategies that Miranda typically uses to build affective alliances with his Twitter followers, for example, how he uses “you” to invoke his audience. I then review his response to hurricane Maria’s landfall in Puerto Rico, including the #AlmostLikePraying benefit song project. I move on to describe how Miranda distances himself from Puerto Rican protest movements, for example, those against austerity measures that took place on May 1, 2018. I argue that comparing Miranda’s responses to these different events points to the limits of cultivating empathy and intimacy on Twitter in order to mobilize activism. This presentation forms part of a larger research project on Latinx creative writers and their use of Twitter.