The Montana State Auditor’s office has proposed fining Mr. Bail and its Billings manager more than $200,000 each for a slew of violations, including those related to a fatal shooting in March in Missoula.
The auditor’s office, which licenses bail bonding companies and bail bondsmen, had been investigating Mr. Bail since October. The notices of proposed agency action issued May 22 state the company and manager Anna Yarbro have “repeatedly” used unlicensed bondsmen.
“In the conduct of its affairs, Mr. Bail employed dishonest practices,” the agency wrote.
The auditor’s office proposed revoking Mr. Bail’s and Yarbro’s licenses and fining the company $280,000 and Yarbro $270,000 for dozens of violations. Mr. Bail has requested a hearing contesting the proposed penalties. Yarbro had not requested a hearing as of Monday afternoon. An attorney for Mr. Bail did not respond to a request for comment.
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Two of the four bail bondsmen involved in the fatal shooting of a fugitive in Missoula earlier this month were unlicensed, having failed the required test numerous times, and the other two had received temporary licenses less than a month before the shooting, according to the Montana State Auditor’s office.
Following the March 4 shooting, the auditor’s office suspended the licenses of Mr. Bail, Yarbro and the two licensed bondsmen involved. The state also ordered Mr. Bail and Yarbro to cease and desist all operations in Montana.
The commissioner’s office began investigating Mr. Bail after receiving a complaint from the Billings Police Department that an administrative assistant for the company was issuing bonds without a license, according to an order from the auditor’s office suspending the licenses.
Yarbro, the manager of Mr. Bail’s Billings office, directed her administrative assistant, Bobbie Helmey, to sell, solicit or negotiate bail bonds even though she does not have a license, the order said. Helmey presented herself as a bondsman and worked in that regard without a valid license, investigators with the auditor’s office concluded.
Helmey applied for a license in July 2025, but the auditor’s office denied the application due to evidence that she had acted as an unlicensed bail agent, according to the proposed fine issued by the auditor’s office May 22. Helmey told investigators that, despite that, Yarbro instructed her to perform bail bond duties and would pay her $25 under the table for each bond she negotiated. Helmey’s Cash App history showed 48 transactions between July 2025 and December 2025, according to the auditor’s investigation. Hemley said Yarbro told her to tell state investigations that she was just “the office girl” and that she never negotiated bonds.
Mr. Bail had also previously dispatched three of the employees involved in the Missoula shooting — Brandon Wakefield, Austin Mistretta and Jorrell Nagel, all unlicensed at the time — along with a licensed bondsman, to enforce a bond in Big Timber in late December, according to the auditor’s office. A complaint about the incident alleged the employees lied about the purpose of their visit, handcuffed and forced a man into their vehicle, demanded payment and threatened to return him to jail, despite not having an active warrant for his arrest.
When investigators interviewed Yarbro about the incident, she refused to identify the agents involved, according to the agency.
On March 4, four Mr. Bail employees — bondsmen Wakefield and Mistretta, who received temporary licenses in February, and unlicensed employees Nagel and Ryan Smith — came to Missoula from Billings to apprehend Joshua Wykle, according to court documents. Video footage showed that the men approached Wykle’s vehicle, parked at the Town Pump on Reserve Street. Mistretta allegedly pointed what appeared to be a rifle at the vehicle, according to the documents. When Nagel was walking behind the Saturn, the car began to reverse. Wakefield then raised his gun into a “shooter’s stance,” court documents allege.
Wykle died at the scene. According to charging documents, the other three men identified Wakefield as the shooter when questioned by responding Missoula police officers. In court filings, prosecutors said Wakefield also told officers that he shot toward the victim.
Wakefield and Mistretta had received their temporary licenses less than a month earlier. Nagel failed the license exam four times since January 2026, and Smith failed the exam twice since February 2026, according to the auditor’s office.
“These dishonest practices put public health and safety at risk,” the auditor’s office wrote in the notice of the proposed fine. “Unlicensed bondsmen have not completed all the necessary training and exams. Using unlicensed bondsmen is a dishonest practice, puts public safety at risk, and is a source of injury and loss to the public.”
The auditor’s office found Mr. Bail violated state law and the associated administrative rules 56 times and is proposing a $280,000 fine. The commissioner may impose a fine of up to $5,000 per violation. The agency is proposing to fine Yarbro $270,000 for 54 violations.
Mr. Bail requested a hearing May 27, but it’s unclear when it will be held. The proceeding will be separate from the hearing scheduled for August appealing the license suspension, according to the auditor’s office.
The auditor’s office late last month also proposed new rules tightening bail bondsmen training and supervision, prompted by the March shooting, said Tyler Newcombe, communications director, in a statement. The office is not issuing any temporary bail bond licenses while it pursues the rule change, he said.
“This office has already taken historic action by suspending the operating authority of Mr. Bail and revoking the licenses of the agents involved,” Newcombe said in a statement. “We are grateful for the opportunity to further safeguard Montanans through a commonsense rule change that will help ensure that inexperienced agents are not engaging in serious situations — unsupervised — where lethal force can be administered.”
As temporary licensees, Wakefield and Mistretta were allowed to operate under the supervision of a licensed bail bond agent while completing their training requirements. According to the auditor’s office rulemaking notice, it does not appear that a fully licensed surety bail bond agent was present in Missoula to supervise Wakefield and Mistretta.
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The state law outlines qualifications for a supervisor but does not define what “supervision” entails.
The proposed rule would require applicants to identify a supervisor, who must submit a sworn affidavit agreeing to comply with the requirements and stating that they meet the qualifications.
Under the rule, a licensed agent may supervise only up to two temporary licensees at a time, and the licensees must be in direct physical presence of the supervisor when apprehending someone or entering a private residence. When a licensee is doing other work, such as issuing bonds, they must be under the direct control and guidance of the supervisor and be able to contact the supervisor immediately. The auditor’s office will hold a hearing on the new rule and amendments June 16. Comments can be submitted through June 24 by calling 406-444-4350 or emailing [email protected].
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