This paper discusses how Iranian musicians navigate continuous crises in successive waves of protest, repression, and war since 2022. I argue that an increasingly radicalized political atmosphere has pressured Iranian artists to take a side in a perceived binary of “overthrow” versus “reform.” This paper centers on the music and reception of Shervin to trace these shifting political conditions shaping music-making in Iran. He first rose to almost instant fame when he released “Baraye” (“Because of”), whose lyrics are a collage assembled from tweets posted under #MahsaAmini, a viral hashtag through which users articulated their reasons to protest during the Woman, Life, Freedom movement. Through rapid circulation, the piece became a sonic emblem of the uprising, even as Shervin was immediately arrested and pressured to delete it from Instagram. This placed Shervin’s subsequent online presence and musical releases under heightened attention. Since then, Shervin has faced not only state surveillance but also close scrutiny from dissident audiences unwilling to tolerate any perceived compromise with the regime—whether in his songs, social media contents, or career decisions such as applying for official permits. Drawing on an ethnography of social media, I ask what it means to sustain a musical persona amid persistent uncertainty shaped by arbitrary state restrictions and shifting public expectations. Building on Miriam Cooke and Lauren Berlant, I listen to the ways that musicians negotiate music-making, dissidence, and the affective politics of contested claim-making in Iran.