Iran has included three important tests within the terms the MOU it is negotiating with the United States. These tests are intended to give Iran's leaders confidence that Trump, a counterparty they see as highly unreliable, is ready to make credible commitments, opening a pathway for further diplomacy.
First, the Iranians are testing the credibility of American security commitments by insisting that the MOU encompasses a Lebanon ceasefire. They are not doing this for the sake of Hezbollah or Lebanese Shias. Rather, they want to see if Trump can restrain Israel in its own backyard. If Trump is able to do that, then he might be able to defend his own deal with Iran from further Israeli sabotage.
Second, Iran is insisting on a nominal fee for vessels passing the Strait of Hormuz. This is not because they want more revenue, which would be negligible. They are insisting on this arrangement because they want to test whether Trump will endorse a deal that includes a clear instantiation of Iranian sovereignty and authority, especially one that did not exist before the war. Iran believes in the logic of a win-win agreement. Trump does not. Forcing him to accept a fee forces him to give Iran a "win" and to defend it as such from the Iran hawks in his circle. This is politically meaningful.
Finally, Iran is insisting on a the release of frozen assets. The sums in question are a tiny fraction of the economic cost of the war and the release of assets is not as valuable as sanctions relief that Iran will also be targeting. But by insisting on the release of funds at an early stage of the negotiations, Iran can test whether broader economic commitments, such as sanctions relief, will be credible. Iran will only consider the promise of sanctions relief to be credible if Trump's sanctions bureaucracy allows Iran to move and spend its own money. The Iranian side will insist on transactions that push the Trump administration to set new precedents for how sanctions relief can be operationalized, especially through guidance to banks.
For many in Washington, these demands seem unreasonable. But that is entirely the point. Iran's leadership won't tolerate a kind of narrow deal that allows U.S. policymakers to avoid putting political capital at stake. Iran wants a deal that reflects the unprecedented nature of the war and ensuing crisis. To meet the moment, the diplomacy has to be transformative.
Iran's leaders don't trust Trump, so they are testing him. So far, he is failing these tests.