Spears has been subject to a conservatorship, or guardianship, since 2008 when she suffered a breakdown. A year later she returned with a new album and world tour and worked solidly until late 2018. Details of her mental health have never been disclosed.
The singer's status as a pop culture icon, and the mystery surrounding her mental health, has focused attention on Wednesday's hearing.
"She was America's sweetheart ... She's a slice of Americana, and her history and watching her troubles and resurrection is also part of the American story," said Scott Rahn, a Los Angeles attorney who specializes in trust and conservatorship issues.
Last year, Spears began the legal process to remove her father, Jamie Spears, from handling personal affairs ranging from her medical care to who visits her secluded villa outside Los Angeles. Her request has still to be considered in detail. Jamie Spears also is a joint conservator of the singer's finances.
The "Piece of Me" singer has never formally requested that the conservatorship be brought to an end. But the New York Times this week said it obtained confidential court documents that showed Spears has been chafing against the restrictions since 2014. She also said she had been forced into a mental health facility two years ago, the newspaper reported.
An attorney for Jamie Spears did not respond to a request for comment on the New York Times report.
"I can only imagine that she's going to address any number of those issues - why it's working, why it's not working, what changes she might like to see," said Rahn.
"She may just be asking to be heard on lifting some restrictions," Rahn said.
Spears, who now communicates to the world through frequent Instagram posts consisting mainly of dance videos, has given no hint of her intentions. But she said last week that she had no idea whether she would ever perform again.
"I'm having fun right now, I'm in a transition in my life and I'm enjoying myself," she added on Instagram. In November she said she was "the happiest I've ever been."
The #FreeBritney fan movement plans a rally on Wednesday near the courthouse to highlight its concerns that the singer is sending cryptic messages through her Instagram platform and is begging to be liberated.
Family law attorney Christopher Melcher says he hopes Spears addresses her fans directly "about whether she is being controlled, whether this is voluntarily impressed upon her, that these are her wishes, (and) to reassure them that she is OK."
(Reporting by Jill Serjeant; Additional reporting by Rollo Ross; editing by Grant McCool) ((firstname.lastname@example.org; 310 491 7279;))