And the whole situation appears to have left him pretty confused.
"We are monitoring him and we know he is still in the country," Elaine Tan, a spokeswoman for the Philippine Bureau of Immigration, told CNN on Thursday afternoon.
Brown's inability to leave has already caused him to miss a concert in Hong Kong that was scheduled for Wednesday night.
The 26-year-old singer used his Instagram account to share his bafflement and frustration about his predicament.
"Can somebody please tell me what the f*** is going on?" he asked in one video that was later deleted. "Cause I don't know, I'm reading headlines after headlines."
In another video, with the caption "Clowning," he appeared to make light of the situation.
"When I go through customs, I'm gonna be just like this, 'Sir, I didn't do nothing,' " Brown said before dropping to the floor and performing a series of comical dance moves.
But by Thursday afternoon, he was giving off a more somber vibe, posting a black-and-white photo of himself looking downcast and captioning it "Mood!"
Brown's visit to the Philippines had appeared to be going smoothly after he performed a concert Tuesday evening in front of a crowd in Manila, the capital.
But that same night, authorities issued an order to stop any attempts by him to leave. It was put in place to compel him to pay money that promoters said was owed to them after he failed to appear for a previous appearance scheduled for last New Year's Eve.
Stopped at airport
Brown was stopped Wednesday morning while preparing to depart on a private jet from Manila's international airport on his way to Hong Kong, the official Philippines News Agency reported.
The Bureau of Immigration says the singer needs to obtain a clearance certificate demonstrating he has no pending obligations in the Philippines before he can leave.
Brown's Hong Kong concert appeared to have been rescheduled for Thursday night, according to one ticketing website in the city. But it was unclear if he was going to make that show.
He is also scheduled to perform in the Chinese territory of Macau on Friday night.
The singer announced earlier this week that a show in Jakarta, Indonesia, scheduled for Saturday was being put on hold because of "safety concerns."
Denied entry to Canada
This isn't the first time the chart-topping star has run into trouble at international borders. In February, he canceled shows in Canada after being denied entry to the country
Brown, an award-winning musician, has a history of bad behavior.
In 2009, he pleaded guilty to assaulting his girlfriend, Rihanna, who is also a hugely popular singer.
He made a public apology but didn't stay out of trouble. In 2012, he had an altercation with rapper Drake at a New York club.
He entered rehab in 2013 to "gain insight into his past and recent behavior," his representative said, only to get kicked out of the facility for smashing his mother's car window during a family session, according to his probation officer.
Brown entered another rehab facility, only to leave in 2014. He was then taken into custody by Los Angeles County sheriff's deputies after a judge revoked his probation. He was released from jail in June 2014.