President Donald Trump embarks Monday on the first major international trip of his second term – an opportunity to shore up relations with a trio of key Middle Eastern allies and prove his might as a dealmaker on the world stage.

American tech and finance CEOs, including Elon Musk, are also expected to be in Saudi Arabia for a government-hosted conference Trump is scheduled to attend as part of his visit.

A series of side deals by the U.S. administration is raising questions about how closely in sync the allies are over major challenges in the region.