But the last couple of days have presented some positive updates that represent hope in the 39-year-old musician's life.
On Sunday evening (UK time), Spears announced she and Sam Asghari are set to tie the knot, by sharing an Instagram video in which she showed off her engagement ring while standing next to her partner who she met in 2016.
"I can’t fucking believe it 💍💍💍💍💍💍❣️!!!!!!" she captioned the clip.
Asghari also shared the engagement news on his Instagram account with a photo of the pair kissing and Spears flashing her finger wearing the sparkler.
Spears was previously married to Kevin Federline from 2004 to 2007, and they share two sons Sean, 15, and Jayden, 14. Before that, she was married to Jason Alexander in 2004 for just 55 hours.
Asghari has supported the singer as she has tried to end the conservatorship.
Things took an unexpected but positive turn last week when her father Jamie Spears, who is the conservator of her $60 million estate, filed a petition to end it.
"As Mr. Spears has said again and again, all he wants is what is best for his daughter. If Ms. Spears wants to terminate the conservatorship and believes that she can handle her own life, Mr. Spears believes that she should get that chance," read part of a court filing obtained by CNN.
On Tuesday, the singer's attorney, Matthew Rosengart, said the news was "another legal victory" for his client.
"This filing represents another legal victory for Britney Spears -- a massive one -- as well as vindication for Ms. Spears," Rosengart said in a statement provided to CNN.
"It appears that Mr. Spears believes he can try to avoid accountability and justice, including sitting for a sworn deposition and answering other discovery under oath," he continued, adding Britney Spears will "continue to explore all options."
The development came after it was revealed last month that Spears' father decided to step down from her conservatorship.
According to a filing in Los Angeles probate court on 12th August, lawyers for Jamie Spears stated that while there are “no actual grounds” for removing him as the conservator of the estate, he feels that the current public battle between him and his daughter is not in her “best interests.”
When Jamie originally led the push to establish Britney’s conservatorship in 2008, he served as both the conservator of her person and estate, but in recent years his role diminished — first, in 2019 when Jodi Montgomery became temporary conservator of Britney's person after Jamie fell ill, and then in February 2021 when a judge approved Britney's team's motion to appoint Bessemer Trust Co. as a co-conservator of her estate.
There have been a recent handful of big changes to Spears' case: namely that she was able to hire her own counsel, Mathew Rosengart, to represent her going forward, and that Rosengart has since been “aggressively” moving to oust her father Jamie Spears from handling her nearly $60 million estate.
In his July 26 motion to replace Jamie with an accountant, Jason Rubin, Rosengart cited Britney and Jamie’s estranged relationship, as well as Jamie’s alleged “potential misconduct” in handling Britney’s fortune, among the many reasons why he should no longer serve as her conservator.