Good morning. The Cayman Islands are home to palm-fringed beaches, endangered iguanas—and $75 billion owed to U.S. life insurance customers. American savers have poured money into life insurance policies and annuities in recent years, making it one of the fastest-growing categories of investments. The companies that manage the money are increasingly storing it offshore, in jurisdictions like the Caymans that don’t require them to hold as much extra capital in case their investments turn sour.

• Transparency problems: They also don’t necessarily have to say who is watching over the money, a lack of transparency that has caught the eye of industry regulators and rating firms and some insurers’ executives themselves. 
   
• Multistep process: The insurers use multistep transactions that rely on reinsurers, entities that provide insurance for insurance companies. The insurers unlock substantial amounts of money that otherwise would be required to backstop policyholders.
   
• No insight: It is exceedingly difficult for insurance customers to know if the money they put away in a policy or annuity has been shifted offshore. They may be advised in small print that a reinsurer is taking over the administration of their policies.
   
• The purpose: Over the past decade, much of the insurance world has been taken over by private-equity firms, which have upended the industry’s boring-but-safe business model. Using armies of lawyers and bankers, they eke out more profit by using offshore reinsurance transactions to free up capital. Supporters of the deals, known as asset-intensive or funded reinsurance, say the freed up capital lets insurers offer better investment returns to customers.

Bessent picks Social Security chief Frank Bisignano as IRS CEO.

Treasury Secretary Scott Bessent has appointed Frank Bisignano to be the chief executive officer of the Internal Revenue Service, creating a new position to help run the beleaguered tax agency.

Bisignano will retain his job running the Social Security Administration while managing the IRS’s day-to-day operations, according to senior administration officials. He will report directly to Bessent, who will remain the formal head of the IRS as acting commissioner. The move lets the administration install a Trump appointee at the IRS quickly without going through the Senate confirmation process.

Bisignano will help implement the administration’s vision for the IRS, which emphasizes upgraded technology and retreats from the heavier enforcement initiatives started under President Joe Biden. He’ll face two immediate challenges: getting ready for the early 2026 tax-filing season and managing a government shutdown. The IRS is fully open for the first five business days of the shutdown using money outside of annual appropriations; it is less certain what happens beyond that.

Heavy truck tariffs to start Nov. 1, Trump says.

The U.S. will impose a 25% tariff on imported medium and heavy trucks beginning on Nov. 1, President Trump posted on Monday.

Trump last month said that tariffs on imported heavy trucks would begin on Oct. 1, but his administration hadn’t yet put the levies into place. Trump previously set 25% tariffs on imported passenger vehicles and light trucks, but the medium and heavy duty truck tariffs are covered by a separate tariff investigation based on national security concerns.

U.S. Supreme Court won’t hear Halkbank appeal.

The U.S. Supreme Court declined to hear a second round of oral arguments from Turkey’s Halkbank over whether the financial institution has sovereign immunity from Justice Department charges that it violated sanctions on Iran, Risk Journal reports.

In a notice posted on Monday, the court said it wouldn’t hear Halkbank’s arguments that common law protections established for foreign sovereigns in previous U.S. court rulings shielded it from the charges.

The bank argued it should receive immunity normally afforded to foreign governments in U.S. courts because Turkey had officially designated it as a repository for Iranian oil-sale proceeds.

Netanyahu enters Hamas talks with broad support at home. Things could still get tricky.

Israeli Prime Minister Benjamin Netanyahu is sending negotiators into Gaza cease-fire talks on Monday with broad support from the Israeli public and backing from his government. He still faces a tricky balancing act of how to end the war and maintain his domestic political support, without giving too much up to Hamas.

Negotiating teams from Israel and the militant group will meet this week with mediators from Arab countries and the U.S. set to begin hashing out a deal to free the hostages still held in Gaza, the first step in President Trump’s 20-point plan for ending the war. The initial talks are expected to focus on hammering out Israeli withdrawal lines and logistics of exchanging Israeli hostages for Palestinian prisoners.

• Thousands of federal agents once tasked with investigating drug smuggling, sexual exploitation and organized crime have been redirected​ to immigration enforcement under President Trump’s second-term push to accelerate deportations, according to current and former officials.
   
• Illinois officials sued Monday to stop President Trump from deploying National Guard forces to Chicago, as the administration’s confrontation with Democratic-led states escalated nationwide.
   
• For Elon Musk, ground zero of the artificial intelligence arms race is a 114-acre tract of grass and swamp on the state line of Tennessee and Mississippi.
   
• The U.S. Supreme Court on Monday declined to hear an appeal from Ghislaine Maxwell, the Jeffrey Epstein confidante who is currently serving a 20-year sentence for sex trafficking.

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