She recently revealed they still have a 'very close friendship' even after his infamous assault on her following a pre-Grammy party back in 2009.
So perhaps it was unsurprising that Rihanna tweeted her support to
Chris Brown ahead of his probation progress court hearing on Monday.
The 24-year-old star wrote to Brown in a direct tweet: 'I'm praying for you and wishing u the best today!' while he then responded: 'Thank u so much.'
And in another more cryptic general tweet, Rihanna wrote: 'Praying for you baby, my best wishes are with you today! Remember that whatever God does in our lives, it is WELL DONE!!!#1 Love.'
However, it is not clear whether she was referring to Brown in the tweet.
But the star's prayers for her former beau were to no avail, with a Los Angeles judge revealing in court that Brown has tested positive for marijuana.
At today's hearing, Judge Patricia Schnegg revealed Brown, who wore a waistcoat and tie and looked sombre, failed a drug test on June 18 in Virginia, where he was fulfilling his court ordered community service, according to TMZ.
Brown then informed his probation officer that he has a medical marijuana prescription in California, the probation report said.
However, Brown failed the test in Virginia, where the drug is illegal - even if you possess a prescription.
Fortunately for Brown, the Judge said that because she had never ordered him not to use drugs, the positive test may not have an impact on his probation.
But she did deliver a stern warning to the star, telling him: 'You are not an average person who can sit in their living room and do what you want to do. You are not only in the public eye, but you are on probation.'
She warned Brown that he needed to be mindful of his public image and his sway with young fans.
'A lot of people look up to you - a lot of kids,' she said. 'What you do and what you say impacts other people.'
Brown stood silently as Schnegg spoke, and at times seemed to nod in agreement.
Meanwhile, the judge told the court that community service logs from Brown's state of Virginia were 'somewhat cryptic' and additional review was needed to determine whether he had complied with his probation.
Brown's lawyer, Mark Geragos, welcomed the inquiry and said he expected to show that Brown had complied with all his probation terms.
A spreadsheet sent by the Richmond, Virginia police chief indicated Brown had completed 1,402 hours of community service, ranging from trash pickup, to washing cars, painting and tending to stables
This year Brown has been involved in several high-profile incidents that have drawn negative headlines including a bottle-throwing New York City nightclub brawl involving his entourage and a group accompanying Drake.
Brown received a cut on his chin, but neither entertainer was charged.
A woman in Miami also accused Brown of taking her cellphone away after she tried to take pictures of him outside a South Beach nightclub, but the singer has not been charged in that incident either.
The judge ordered Brown to return to court on November 1 for another update and asked officials to prepare a supplemental probation report on Brown.
Virginia officials also reported that Brown may have traveled to Paris without permission, but Schnegg said she has approved most of the singer's travel and would have to review that claim further.
In an interview with Oprah Winfrey earlier this year, Rihanna said she was angry at Brown but also felt protective of him.
'Nobody's going to say he needs help. Everybody's going to say he's a monster, without looking at the source. I was more concerned about him.'
The singer confirmed they still have a 'very close friendship' and added she felt sympathy for him in the wake of the infamous violent attack that left her in hospital.
She explained: 'I just felt like he made that mistake because he needed help. The main thing for me is that he is at peace. I'm not at peace if he is unhappy or he is still lonely.I care. It actually matters that he finds peace.'
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