O'Connor released his third studio album, Pony (2019), lyrically exploring more personal topics, such as human emotion, and experimenting with different genres.

[7] Upon listening to the album, fellow English musician and producer Two Inch Punch got in touch with him, providing him with a management team.

[14] His work was compared by Aimee Cliff of The Fader in 2017 to "other artsy, post-genre teen artists, such as Kevin Abstract or Steve Lacy".

[15] O'Connor's first release following the success of Apricot Princess and Flower Boy was on 11 October 2017 with the single "Loving Is Easy", created in collaboration with the Dutch artist Benny Sings.

[13] On 9 October 2018, O'Connor was scheduled to appear on the French television programme Quotidien, but refused to perform because it featured a sketch by comedian Alison Wheeler parodying the Ku Klux Klan, which he called "tasteless".

On 13 January 2022, he began officially teasing the album, sending out postcards containing a phone number that when called, a snippet of a song would play.

[25][26] In July 2022, O'Connor cancelled tour dates in Australia, New Zealand and Europe due to "unforeseen personal circumstances".

Growing up, O'Connor listened to Queen, ABBA, Stevie Wonder, and American alternative artists like Weezer and Green Day.

[35] On 10 October 2022, O'Connor appeared in Southwark Crown Court and was charged with six counts of sexual assault of the same woman, alleged to have taken place in June 2021.

A representative for O'Connor released a statement on his behalf which read: "Alex is shocked by the allegations, which he denies, and looks forward to clearing his name in court.

[36] On 22 December 2022, O'Connor released a statement saying all charges against him were dropped and the case was to be dismissed following an investigation by the Crown Prosecution Service.

O'Connor claimed in his statement that CCTV footage and a police interview with the complainant's partner – who was with her on the night in question – did not match her account, meaning the case did not meet the CPS's legal test for a prosecution.