VATICAN CITY (AP) — Pope Francis’ apology Tuesday for using a vulgar term to refer to gay men was the latest comment to make headlines about the Catholic Church’s teachings on homosexuality.

Francis has made a hallmark of reaching out to LGBTQ+ Catholics, but his 11-year pontificate has also seen plenty of problems arise over his informal way of speaking and his outreach, evidence of how fraught the issue is for the church.

Officially, the Catholic Church teaches that homosexual people must be treated with dignity and respect, but that homosexual activity is “intrinsically disordered.” It also says that men who “practice homosexuality, present deep-seated homosexual tendencies or support the so-called gay culture” cannot be ordained.

Here is a look at some of Francis’ most noteworthy comments.

— July 30, 2013. During his first press conference, says “Who am I to judge?” when asked about a purportedly gay priest, signalling a more welcoming approach to LGBTQ+ Catholics.