Whether Kanye West wins his $10 million lawsuit against Lloyd’s of London over canceling shows on his 2016 The Life of Pablo tour depends on his medical history and how much he was willing to pay to make up for the risk, several concert-insurance experts say.

“If the artist has a bad reputation for canceling concerts, then it’s likely they’re going to have more exclusions and higher premiums,” says Elizabeth Leontieff, chief operating officer of SteelBridge Insurance in Santa Cruz, California, which insures concerts and festivals. “The insurance company is not in the business to lose money — they’re pretty careful when they write these policies to make sure they’re not going to have to pay anything.”

In the suit, West’s doctor acknowledges the rapper “suffered a debilitating medical condition” that forced him to cut off two concerts and cancel the rest of the tour; West revealed in court documents that he subsequently checked into UCLA’s Neuropsychiatric Hospital Center for eight days. West’s touring company, Very Good, filed a claim two days after the cancelation, and his lawsuit alleges Lloyd’s has withheld payment.

Typically, when a major artist begins a tour and seeks cancelation insurance, the insurance company investigates the artist’s medical history to assess the risk. Lloyd’s, for example, extensively looked into Michael Jackson, who had a history of drug use, medical problems and high-profile concert cancelations, before his ill-fated This Is It tour in 2009, demanding medical records and examinations and charging $17.5 million for coverage.

It’s unclear if West had a history of mental or physical illness before canceling the tour. “[Lloyd’s] do not like to pay out on cancelation claims for medical reasons, especially when the underlying reason is psychological or exhaustion as opposed to what they consider ‘real’ reasons like severe flu or bodily injury,” says a concert-business source. “Given Kanye’s touring history and volatility, I doubt he will collect the full $10 million.”

Insurers and promoters are divided over Lloyd’s history in reimbursing concert-cancelation claims. “They never pay,” says John Scher, a longtime New York promoter. “I don’t know exactly the conditions under Kanye’s claim, but my guess is they just don’t want to pay.” But Peter Tempkins, managing director for entertainment for Hub International, a Nashville insurance company, says Lloyd’s has paid out numerous claims over the years. “Lloyd’s actually does pay — unless they feel that something is amiss,” he says. “Sometimes you have to fight to nudge them in the right direction.”

A rep for Lloyd’s declined to comment on West’s case but e-mailed a statement to Rolling Stone. “The reputation of the market has been built on meeting our obligations quickly and effectively where a claim should be settled,” the rep says. “In the last year alone we paid out over £14 billion in claims. The market will always take steps to find a solution amicable to both clients and insurers where there are disagreements through discussion and mediation. However, where an agreement cannot be reached, valid claims can only be paid on syndicates being satisfied that they have the information required to make any payment.”

A rep for West did not return a request for comment.

But West’s breach-of-contract lawsuit, filed last week, may never make it to court. “Since the last thing Kanye wants to have to do is testify, either in court or through deposition, my guess is this is a strategic attempt to get [the] Lloyd’s companies to settle,” says one industry source. Adds Leontieff: “Very few insurance claims go to court. They usually settle.”