2014: Robbery charge and juvenile detention

In late 2014, Gaulden was arrested for robbery and sent to a detention center in Tallulah, Louisiana. He was released after serving 6 months.[177][178][158]
2016–2017: Attempted murder

On November 28, 2016, U.S. Marshals arrested Gaulden before a concert in Austin, Texas, accusing him of jumping out of a vehicle and opening fire on a group of people on a South Baton Rouge street. Gaulden was charged with two counts of attempted murder.[179][180] Gaulden was in jail until May 2017 for attempted first degree murder.[181] Speaking on his incarceration, he said "I don't think they really target, but if you got a name, they know who you is, you do something, they gonna come get you, and whoever you're with and whatever they do, you're accountable for it just because you got the biggest name. That's how that ♥♥♥♥ go."[182] Facing two counts of attempted first-degree murder, he pleaded guilty to a reduced charge of aggravated assault with a firearm. On August 22, 2017, he was sentenced to a suspended ten-year prison term and three years of active probation.[180]
2018: Assault, weapons and kidnapping
Gaulden's 2018 mugshot

Gaulden was arrested before a concert at The Moon nightclub in Tallahassee on February 25, 2018. Gaulden had a warrant in the state of Georgia for allegedly committing assault, weapons violations and kidnapping.[183] Hotel surveillance footage leaked shortly following his arrest showing Gaulden assaulting his former girlfriend.[184] On March 15, 2018, he was released from jail on $75,000 bail.[185]
2019: Assault and battery lawsuit

On March 12, 2019, it was reported that Gaulden and Never Broke Again artist Tyquian "Quando Rondo" Bowman were filed suit by a man claiming to be the rappers' bodyguard, tour manager and/or tour DJ for assault, battery and emotional distress. The lawsuit claims that on December 21, 2018, during a concert in Florence, South Carolina, the two performers were annoyed by a crazed fan resulting in an argument. The claimant states that he, Gaulden, Bowman and members of their entourage were escorted backstage by management, venue owners and concert organizers where he claims to have been assaulted by the two aforementioned. The person, who claimed was confronted by the two defendants, commented that Bowman (although unprovoked) instigated the incident by attempting to force him back onstage to break up the fan craze to secure his team, but after he refused, Bowman and Gaulden immediately assaulted him as he tried to explain to both parties of his deeds. It resulted in the victim sustaining a "cracked tooth, bloody face and injuries to his reputation". Gaulden's attorney stated that he had no prior knowledge of the incident, but would look into the outcome of the lawsuit.[186][187][188][189][190][191]
2019: Miami shooting, probation violation, and house arrest

While Gaulden was on probation, on May 12, 2019, he was involved in a shooting in Miami in which he returned fire after a shooter in a black Cadillac Escalade opened fire, injuring Gaulden's girlfriend and killing a bystander.[192] Though Gaulden's charges for the shooting itself were dismissed, he was found to be in the company of Ben Fields and Trulondrick "Boomer" Norman, which violated a special condition of his probation; for this violation, the judge ordered him to spend 90 days in jail, banned him from performing for the next 14 months, and sentenced him to house arrest with electronic monitoring for the remainder of his probation.[193]
2019–2020: Probation termination and renewal

On December 13, 2019, the judge officially terminated Gaulden's probation for two counts of attempted murder.[194] However, he was sentenced to a year of probation five days later after he pleaded guilty to simple assault in the case involving his ex-girlfriend.[195]
2020: Baton Rouge arrest for federal firearm and drug offenses

On September 28, 2020, Gaulden was among sixteen people arrested in Baton Rouge, Louisiana on various charges, including distribution and manufacturing of drugs and possession of stolen firearms. His lawyer denied any guilt, stating "There was no indication that he had any guns or drugs on him at the time of the arrest".[196]
2021–2022: California federal firearm charge and Baton Rouge federal firearm and drug charge
Gaulden's 2021 mugshot

On March 22, 2021, Gaulden was arrested by federal agents in Los Angeles executing a federal warrant stemming from his September 2020 arrest in Baton Rouge. Officers attempted to stop a vehicle with Gaulden in it to serve the warrant when Gaulden took off on foot. After a search that involved using a police dog, Gaulden was found and booked on federal firearms charges.[197][198] On October 26, 2021, he was released from jail on a $1.5 million bail.[199]

On February 24, 2022, following Gaulden's September 2020 Baton Rouge arrest in the process of recording a music video, Gaulden's team filed a motion to suppress the firearm obtained during the arrest alongside the video and photo evidence via an SD card from the video shoot for "Chopper City". On March 2, 2022, the motion to suppress the video evidence was granted, however, the motion to suppress the firearm was denied.[196][200][201][202] Following Gaulden's win, a trial date was set for May 16, 2022, however, it was later pushed back due to unforeseeable actions.[203] In June 2022, Gaulden's team won a pre-trial motion as his team filed for a removal of evidence due to prosecutorial misconduct.[204]

During the trial for Gaulden's California federal firearm charge, on July 12, 2022, the prosecution’s motion for allowing lyrics from Gaulden's "Life Support" and "Gunsmoke", in both of which YoungBoy raps about FN Herstals, in the trial against him was denied.[205][206][207][208][209][210][211] On July 15, 2022, Gaulden was found not guilty of his federal firearms charges from California, due to a lack of evidence linking him to intentionally possessing the weapons found.[212][213][214][215][216][202]
2023–2024: Baton Rouge federal firearm charge

On March 9, 2023, regarding Gaulden's Baton Rouge federal firearm charge, the prosecution team filed a motion to challenge Gaulden's motion to suppress the video and photo evidence – which they won in March 2022. It was noted that the three-judge panel would come to a decision in the following weeks.[217]

On March 15, 2023, it was announced that Judge Shelly ♥♥♥♥ lifted restrictions from Gaulden's house arrest. In the report, two conditions were removed. Firstly, Gaulden would be allowed to have more than three visitors at a time without a curfew restriction.[218][219]

After the prosecution team in Gaulden's Baton Rouge case filed a motion to challenge his to suppress the video and photo evidence, in July 2023, Gaulden's team re-filed with the United States courts of appeals, however, he lost the appeal.[220] In October 2023, regarding Gaulden's Baton Rouge federal firearm charge, after Gaulden's team challenged the lost appeal, the United States Court of Appeals for the Fifth Circuit reversed their decision, allowing the prosecution to use the evidence.[221]

In November 2023, Gaulden's defense filed a motion in order to amend his pre-trial conditions due to police corruption.[222] Later that month, the court denied Gaulden's motion to ease his house arrest limitations due to his diminishing mental health alongside declining music sales.[223] Assistant US attorney William K. Morris stated that Gaulden's "current conditions of pre-trial release prohibit him from seeking and obtaining mental health treatment".[224] On December 19, 2023, Billboard announced that Judge Shelly ♥♥♥♥ denied Gaulden's request to obtain more recording studio access, however, she allowed the rapper to get better medical treatment.[225]

On March 13, 2024, a Utah federal court held up the case, due to Gaulden's attorney filing for Second Amendment