This chapter examines how heterocringe humor—an online practice similar to meme pages which aims to poke fun and criticize straight people and heteronormativity by sharing cringe heteronormative content found on the internet—discursively manages the risk of humor failure caused by the transgressive nature of this content. Using critical and multimodal discourse analysis, this study investigates a corpus of 2807 Instagram posts from the now banned @heterocringe and @german_hetero_cringe accounts. Relying on Bell’s (2015) framework on failed humor two main strategies emerge from the analyses: prevention strategies to secure the success of heterocringe humor and strategies expressing non-appreciation of heterocringe humor. Although discriminatory discourses concerning members of the LGBTQIA + community seem to trigger both preventive reactions and non-appreciation, indignation happens mostly regarding virulent misogynistic content. Through these analyses, this study highlights the political goal of heterocringe humor on Instagram.