This article examines how the UK press regulators balance freedom of expression against protecting transgender people from discriminatory reporting amid the growing polarisation over trans rights.  It provides the first comprehensive analysis of IPSO’s and IMPRESS’ rulings on trans-related complaints, offering novel insights into the intersections of news production, audience reception and press regulation. The research reveals that IPSO’s myopic approach overlooks the prejudicial nuances in humour, visuals and the interplay between inaccuracy and discrimination, allowing dominant trans stereotypes criticised in the Leveson Report to persist. Conversely, IMPRESS’ engagement with trans issues is very limited compared to IPSO’s but its newly-adopted ‘discursive harm’ model is a promising step in the right direction. The paper concludes that it is only by prioritising the standpoints of marginalised trans people and firmly incorporating these into journalistic practices and press regulation that news media can contribute constructively to the public dialogue over trans inclusion.