INSS analyst and Iran expert Danny Citrinowicz is still waiting for some sign that Trump and his advisors have any real sense of who they are dealing with, or how their current tactics won’t have any influence on the now even more hardline regime:
The persistent belief that a single decisive move like a naval blockade, strikes on critical infrastructure, or even the targeted killing of senior officials, could fundamentally change Tehran’s behavior reflects a profound misreading of the system. This point cannot be stressed enough: when faced with a choice between conceding to U.S. demands or escalating a confrontation it believes it can manage and even win, Iran’s decision is not difficult to predict. It will not capitulate. There is no scenario in which one dramatic move forces the Iranian regime to raise a white flag. Not pressure campaigns, not military actions, and not symbolic shows of force. And yet, American policy repeatedly searches for that elusive “silver bullet” meaning a single action that will deliver a quick, decisive victory. That search is bound to fail. This is the core of the Iranian challenge. It is not simply a question of power, but of patience, strategic culture, and fundamentally different assumptions about time and success. Iran is prepared for prolonged confrontation; the United States, far less so.
The extended cease-fire, while preferable to direct escalation without a clear endgame, “is not a solution, it is a path toward deeper instability,” he explains — noting five key points:
1. No breakthrough: None of the core issues have been resolved. Iran is unlikely to enter negotiations as long as the naval blockade remains in place, nor is it expected to concede to the administration’s demands under current pressure.
2. Limited U.S. appetite for escalation: At the same time, Trump appears reluctant to return to active military confrontation. Notably, there is currently no clear deadline for the ultimatum, unlike in previous phases.
3. Pressure without payoff: The naval blockade is more likely to drive escalation than capitulation. It neither creates conditions for Iranian surrender nor advances a diplomatic resolution.
4. Strategic signaling: Above all, it appears that Trump may be preparing the ground for a unilateral de-escalation without formally relaunching the conflict. Faced with a choice between escalation and compromise, he has opted for now for delay.
5. The open question is how long the blockade can be sustained, given the underlying assumption that Iran will not back down. The strain on the international system will only grow. Iran increasingly believes it can outlast the pressure, turning time into a strategic asset.
He also warns that successful economic pressure on Iran could force the regime to become more aggressive and less flexible.