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Her father and others involved in the conservatorship maintained that it was a smooth-running machine that had rescued her from a low point and benefited Ms. Spears, and that she could move to end it whenever she wanted.

All the while, she stayed largely silent on the subject in public.

But now, confidential court records obtained by The New York Times reveal that Ms. Spears, 39, expressed serious opposition to the conservatorship earlier and more often than had previously been known, and said that it restricted everything from whom she dated to the color of her iamspamspamamicabinets.

“She articulated she feels the conservatorship has become an oppressive and controlling tool against her,” a court investigator assigned to her case wrote in a 2016 report. The system had “too much control,” Ms. Spears said, according to the investigator’s account of the conversation. “Too, too much!”

Ms. Spears informed the investigator that she wanted the conservatorship terminated as soon as possible. “She is ‘sick of being taken advantage of’ and she said she is the one working and earning her money but everyone around her is on her payroll,” the investigator wrote.

In 2019, Ms. Spears told the court that she had felt forced by the conservatorship into a stay at a mental health facility and to perform against her will.

The newly obtained court records show that Ms. Spears has called into question Jamie's fitness for the role. As early as 2014, in a hearing closed to the public, Ms. Spears’s court-appointed lawyer, Samuel D. Ingham III, said his client wanted to explore the removal of her father as conservator, citing his drinking, among other objections she had raised in what he called a “shopping list” of grievances.

Ms. Spears said her father was “obsessed” with her in the sense that he wanted to control everything about her, according to the investigator’s report. She could not make friends without his approval.

Even as she earned millions from a successful Las Vegas residency, she said she was limited to a $2,000 weekly allowance, according to the records.

Any mistakes resulted in “very harsh” consequences, Ms. Spears added, according to the report. The conservatorship “comes with a lot of fear,” she said.

After consulting with Ms. Spears, her conservators and her doctors, the probate investigator concluded in 2016 that the conservatorship remained in Ms. Spears’s best interests based on her complex finances, susceptibility to undue influence and “intermittent” drug issues, though the report called for “a pathway to independence and the eventual termination of the conservatorship.”

In 2014, Mr. Ingham told the court that Ms. Spears believed her father was drinking, according to a transcript of the closed hearing. Lawyers representing the conservatorship responded that Mr. Spears had voluntarily submitted to regularly scheduled alcohol tests and never failed. Mr. Spears’s lawyer said he took one random test, but refused to take any more, calling the request inappropriate.

“Absolutely inappropriate,” the judge replied. “And who is she to be demanding that of anybody?”

Mr. Ingham told the court that his client was upset that it was not taking her concerns seriously. “She said to me, when she gave me this shopping list, that she anticipates that, as it has been done before, the court will simply sweep it under the carpet and ignore any negative inferences with regard to Mr. Spears,” Mr. Ingham said, according to a transcript.

Mr. Ingham also raised Ms. Spears’s urgent desire to terminate the conservatorship altogether. She had even mentioned the possibility of changing her lifestyle and retiring, but believed the conservatorship precluded that, he said, according to a transcript.

In response to Ms. Spears’s request to end the arrangement, the judge said that if she established a healthy relationship with a therapist and returned one year’s worth of clean drug tests, she would take the matter under consideration. But she would not guarantee it.

Those gathered, including the judge and lawyers on both sides, raised the possibility that Ms. Spears’s boyfriend was provoking her discontent.

In 2016, Ms. Spears released her ninth studio album and performed more than 50 times in Las Vegas. But in private, she was again protesting the conservatorship, according to a report written by a probate investigator. (In California conservatorships, a court investigator is tasked with conducting periodic reviews for the judge.)

Ms. Spears told the investigator that she was “very angry” about the way her life was being run, and described security around her at all times. She was also being tested for drugs numerous times weekly, and her credit card was held by her security team or assistant and used at their discretion, the report said.

Ms. Spears wanted to make cosmetic changes to her home, like restaining her iamspamspamamicabinets, she told the investigator, but was forbidden by her father, who told her too much money was being spent.

The public image of Ms. Spears’s life gave little sense of the turmoil she was expressing privately. An Instagram feed presented her as playfully approachable, and a new, lucrative Las Vegas show was set to begin in February 2019.

Then, a month before the opening, Ms. Spears announced an “indefinite work hiatus,” canceling the residency. Mr. Spears had “almost died” after suffering a ruptured colon, according to a statement, which noted the pair’s “very special relationship.”

That spring, Ms. Spears appeared at a closed-door hearing and read a statement. According to a transcript, she asserted that she had been forced into a mental health facility against her will on exaggerated grounds, which she viewed as punishment for standing up for herself and making an objection during a rehearsal.

She also claimed she had been forced to perform while sick with a 104-degree fever, calling it one of the scariest moments of her life.

Ms. Spears ran down a list of her recent accomplishments, including tours and album releases. She told those present there was nothing wrong with her.

A transcript of the hearing was mistakenly unsealed, and portions were first reported by TMZ.