Sean Kingston Asks Court for Permission to Perform at Summerfest While Awaiting Sentencing

R&B star Sean Kingston is hoping to get back to work, but legal troubles are standing in his way.

Kingston — whose real name is Kisean Paul Anderson — filed a motion asking a Florida judge for permission to leave the state for one night so he can perform at Milwaukee’s Summerfest on June 20, 2025. The request comes just weeks after Kingston was found guilty on multiple counts of wire fraud.

According to court documents, Kingston was convicted on March 28, 2025, of conspiracy to commit wire fraud and five counts of wire fraud. Despite being released on a $500,000 surety bond and $100,000 cash bond, the judge restricted his travel and placed him on home detention with GPS monitoring.

In his motion, Kingston’s legal team argued that the singer hasn’t been able to earn income since being confined to South Florida. They said the Summerfest performance isn’t a nightclub gig, but rather a festival concert that would allow him to fulfill prior commitments and financially support himself.

“Mr. Anderson is going through a difficult time,” the filing states. “He is hoping the Court will allow him to travel only for work purposes.”

The singer promised to share his full itinerary with probation and follow any rules set by the court, including checking in before and after travel.

But not everyone is on board. Prosecutors and Kingston’s probation officer have objected to his request, according to the motion.

As of now, it’s up to the judge to decide whether Kingston will get a brief break from house arrest to return to the stage — or if his legal woes will keep him grounded a little longer.

Kingston is scheduled to be sentenced on August 15, 2025, which could determine his future beyond just music.