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This paper examines the use of digital media by Asian Americans for explicitly activist aims, looking at how the technological affordances of online tools intersect with the cultural and political practices of real communities. In particular, I focus on a series of Twitter campaigns that centered on images of Asian Americans in the media. Through tracing the different conversations that took place around the hashtags #HowIMetYourRacism, #NotYourAsianSidekick, and #CancelColbert, we can more clearly see the way that media provides both a rallying point for activism and a means for shifting conversations to what it is that really matters—the place of Asian Americans in American society. I look at the impact of cultural formations, political identities, and affective relationships on how new media technologies are taken up as part of Asian American media activism. Within the efforts of Twitter activists and participants we can better understand the possibilities for using new media to generate a form of politicized participatory culture for Asian Americans online. I argue that even when media activism is seen to “fail,” the dialogues fostered through Twitter hashtags serve to illuminate the connection between engagement with problematic images and the fight for cultural citizenship.