Montana auditor proposes steep fine for Mr. Bail following fatal Missoula shooting

The Montana state auditor's office wants to fine Billings bail company Mr. Bail and its manager more than $200,000 for over 50 violations, including some related to a fatal Missoula shooting involving some of its bond agents.

The state regulator filed the proposed action to fine Mr. Bail on May 22. The company has been under investigation since October for alleged repeated use of unlicensed bond agents by the office of James Brown, Montana's Commissioner of Securities and Insurance as well as its auditor.

In March of this year, Missoula prosecutors allege, one of Mr. Bail's agents, Brandon Wakefield, shot Joshua Wykle, a client of Mr. Bail whom Wakefield and three other agents were there to arrest. Wakefield has been charged with deliberate homicide, and another agent, Austin Mistretta, has been charged with attempted assault.

Brown's office received a complaint in October 2025 that a Mr. Bail employee was conducting bail transaction without a license, according to the filing.

The state auditor's office investigated these allegations and found that they were true: Mr. Bail office assistant, Bobbie Hemley, had been advertising herself as a bail agent, the filing states.

In January 2026, the auditor's office received a complaint that Wakefield, Mistretta and two other Mr. Bail agents had handcuffed and detained a man who didn't have an active warrant, demanding payment from him and refusing to identify themselves. Wakefield, Mistretta and one other agent involved, Jorrel Nagel, were unlicensed at the time. Nagel was also present at Wykle's shooting, the filing states, still unlicensed as he had failed the exam four times since.

The fourth agent present at Wykle's shooting, Ryan Smith, also did not have a bail bond license because he failed the exam, the filing states.

According to the filing, Hemley reached out to CSI in March, alleging that Anna Yarbro, Mr. Bail's manager, had paid her $25 under the table for each bond she negotiated. She provided investigators her Cash App history, showing 48 transactions from Yarbro totaling almost $7,000. Hemley told CSI she was instructed to tell investigators she hadn't conducted bond work, and Yarbro fired her after her interview with CSI earlier that year.

The auditor may fine agencies $5,000 per violation of Montana insurance code, the filing states. The commissioner is proposing a fine of $270,000 for 54 violations across the multiple incidents since October 2025. Additionally, the filing moves to permanently revoke the license of Mr. Bail and Yarbro.

On May 22, Yarbro requested a hearing on these proposals. The matter will be decided by Stuart Segrest with the Christensen & Prezeau law firm in Helena, who has been designated special deputy insurance commissioner.

The hearing has yet to be scheduled. Yarbro is also appealing the suspension of her and Mr. Bail's licenses, with a hearing set for Aug. 14.

The auditor's office is also currently proposing stricter rules surrounding licensing and supervision of bail bond agents.