In August 2018 he organised a concert featuring Jamaican dancehall reggae artiste Charly Black.  On December 21, 2018, he organised the second coming of Morgan Heritage in what was dubbed the Jamaica-Africa Tour at the Harare International Conference Centre (HICC). The show was criticised by Fred Zindi who interviewed people such as Clive Mukundu who said the sound was terrible whilst Winky D's manager Jonathan Banda who also confirmed the sound was terrible and that the stage was not even set for a live performance. He also added that Boss Dhama made some unacceptable demands which saw Winky D and another band Transit Crew not performing. 
On 5 January 2021, Dhama pleaded guilty and admitted to “partaking and contravening a public gathering during a national lockdown period” when he appeared before Harare provincial magistrate Vongai Guwuriro together with his co-accused DJ Fantan and Levels. He was remanded in custody pending bail ruling on 6 January 2021.
Dhama and his co-accused were found guilty and jailed for six effective months for violating the Covid-19 regulations.
Harare provincial magistrate Vongai Guwuriro had initially jailed the trio for 12 months before setting aside six months of the sentence.
The six months were set aside for three years on condition that they will not commit a similar offence during that period.
- Charly Black to meet fans in ghettos, NewsDay, Published: July 18, 2018, Retrieved: January 4, 2021
- Fred Zindi, Morgan Heritage duped Zimbabwe, The Standard, Published: January 13, 2019, Retrieved: January 4, 2021
- Nyore Madzianike, JUST IN: DJ Fantan, Levels, Dhama appear in court, The Herald, Published: January 5, 2021, Retrieved: January 5, 2021
- DJ Fantan, Levels, Dhama jailed six months, The Chronicle, Published: January 6, 2020, Retrieved: January 6, 2020