On 22 April 2019, Kyagulanyi was detained while attempting to make his way to a planned concert at his private club in southern Kampala, which was cancelled by police. He was accused of leading a protest in the city the previous year without prior police authorisation; the protest was held against the "social media tax" which took effect in July 2018. On 29 April 2019, on his way to the offices of the Criminal Investigations Directorate (CID) to honour a summons and provide a statement on the cancelled concert, Kyagulanyi was again arrested and taken to Buganda Road Court, where he was charged with disobedience of statutory duty and remanded to Luzira Maximum Security Prison until his bail hearing on 2 May. In a statement the following day, Amnesty International demanded his immediate release and urged the Ugandan government to "stop misusing the law in a shameless attempt to silence him for criticizing the government." On the day of the hearing, which was conducted via video conferencing (the first time in the history of Uganda's justice system), Kyagulanyi was granted bail and released from prison, with the court also barring him from holding unlawful demonstrations.
