Donald Trump has played this hand before during the 5-month-old Iran war.

It starts with a grim warning to Tehran that he’s on the cusp of ordering U.S. forces to “obliterate” its power plants or seize key parts of its oil industry if its leaders don’t quickly agree to U.S. terms to end the war. It ends with him edging away with a last-minute declaration, sometimes at the behest of Gulf allies, that he’s going to give diplomacy more time.

The hardball strategy — one that Trump honed during his years competing in New York’s real estate scene and has employed in politics — aims to create movement in negotiation through pressure and chaos. But the tactic is facing a challenge with an Iranian theocracy that believes it holds a higher threshold for strategic pain than Washington.