This article advances a deeply political and material understanding of feeling in the context of racial capitalism. Informed by Ahmed's work on the "politics of good feeling" (2008, 1) and Gilmore's concept of "infrastructure of feeling" (2022, 490), we interrogate how feeling is regulated in everyday literacy contexts through two examples: 1) the history of the phrase "joy of reading" and its use in a text for teachers and 2) a vignette in which youth were expected to use digital media to share their grief. Both examples show how liberal sentimentality works to control unruly or unhappy feelings that disrupt the democratizing fiction of white progressivism. With a deeper understanding of the infrastructure of feeling as an analytic intervention drawing on liberatory histories and struggles, educators can work to transform these spaces into arenas of emotional negotiation and emancipation, thereby countering the oppressive reach of racial capitalism.