Donald Trump’s war with Iran may be entering its most dangerous phase yet.

American forces are still striking targets. U.S. military power remains overwhelming. But according to retired Lt. Gen. Mark Hertling, Tehran is increasingly shaping the conflict on its own terms—while the United States absorbs military losses, diplomatic damage and mounting economic pain.

His conclusion was ominous:

Iran currently has the “upper hand.”

Speaking Monday on Deadline: White House, Hertling argued that the conflict cannot be understood simply by counting airstrikes or destroyed targets.

The more important question is whether either side is achieving its broader strategic goals.

By that measure, he said, the war is not going well for Washington.

The assessment followed another Pentagon announcement involving U.S. service-member deaths, while a ceasefire reached only weeks earlier appeared to have collapsed.

The Trump administration has continued expanding military operations without publicly defining a clear path toward victory, a lasting settlement or withdrawal.

Hertling called that situation “tragic.”

“You’ve got to take a look at the operational campaign of both nations,” he said.

The retired general explained that the United States had shifted beyond attacking individual weapons systems.

American forces were now targeting the infrastructure that allows Iran to rebuild and sustain military power.

That reportedly includes transportation networks, bridges, fuel-distribution sites and strategically important locations around Bandar Abbas and Isfahan.

The objective, Hertling said, is to weaken Iran’s ability to regenerate its forces while increasing pressure on the country’s leadership and population.

Washington apparently believes that deep divisions exist among the Islamic Revolutionary Guard Corps, Iran’s clerical leadership and ordinary citizens.

By damaging economic and logistical systems, the administration may hope to widen those divisions and reduce public willingness to continue the war.

In theory, enough pressure could force Tehran back to the negotiating table.

The United States would then use military force to produce a political concession.

But Iran is not merely waiting to be overwhelmed.

It has its own campaign.

“They’re keeping the Strait [of Hormuz] closed,” Hertling said.

That single point carries enormous global consequences.

The Strait of Hormuz is one of the world’s most important energy routes. Disruption there can restrict oil shipments, raise insurance costs and send crude and gasoline prices sharply higher.

Even without a permanent closure, continued uncertainty can shake international markets.

That means Iran can impose pain far beyond the battlefield.

American consumers may experience the war through more expensive fuel, transportation and goods.

European and Asian economies dependent on energy shipments can also feel the pressure.

The conflict therefore becomes a test of how much economic disruption the United States and its allies are prepared to tolerate.

Hertling also warned that Iran is working to drain U.S. military resources.

American forces in the region depend heavily on advanced air-defense systems to intercept missiles and drones.

Those systems use costly and limited interceptor inventories.

If Iran and its proxies continue launching repeated attacks, they can force the United States to expend defensive weapons faster than they can easily be replaced.

That strategy does not require Iran to defeat the U.S. military directly.

It only needs to make the campaign increasingly expensive, exhausting and politically difficult.

Every missile intercepted costs money.

Every defensive system moved to the region may be unavailable elsewhere.

Every prolonged deployment places additional stress on troops, equipment and military planning.

Iran can lose aircraft, launch sites and facilities while still achieving its objective if the United States becomes trapped in an open-ended confrontation.

Hertling said Tehran is also attempting to divide Washington from regional allies.

He specifically referred to tensions involving Jordan, Qatar, Kuwait and the United Arab Emirates.

Those governments may cooperate with the United States on security while simultaneously fearing retaliation, domestic unrest and economic disruption.

The longer the war continues, the more difficult that balancing act becomes.

Regional partners may resist allowing U.S. operations from their territory.

They may demand limits on the campaign.

They may distance themselves publicly from Washington to reduce political pressure at home.

Iran does not have to transform those countries into allies.

It only needs to make their cooperation with the United States more uncertain.

That weakens Washington’s freedom of action.

It complicates logistics and basing.

It also damages the appearance of a unified coalition.

Hertling argued that Iran understands another American vulnerability:

Public reaction to military deaths.

“They are hurting us tactically because they know that the U.S. will focus on individual combat deaths,” he said.

That statement does not diminish the significance of those deaths.

It recognizes that each casualty can reshape public opinion in a democracy, particularly when the government has not clearly explained the mission or end state.

Americans may initially support limited military action.

Support can erode quickly when service members continue dying and the administration cannot explain when the fighting will stop.

The Trump administration now faces that question.

What would victory look like?

The destruction of Iran’s missile capability?

A new nuclear agreement?

The collapse of the government?

The reopening of the Strait of Hormuz?

The administration has not publicly established a single, measurable objective that would clearly end the conflict.

Without such an objective, every new operation can create the need for another.

Destroyed infrastructure is rebuilt.

Proxy forces retaliate.

New targets emerge.

Temporary successes become reasons to extend the war rather than conclude it.

Hertling warned that Iran is opening additional fronts through allied armed groups.

He highlighted the Houthis and the Bab el-Mandeb Strait, another critical maritime chokepoint connecting the Red Sea to the Gulf of Aden.

If attacks or blockades significantly disrupt that waterway, international shipping could face pressure at two strategic routes simultaneously.

The consequences could include higher freight costs, delays, rising insurance premiums and further energy-market instability.

Those costs would eventually reach ordinary consumers.

Goods imported by ship become more expensive.

Manufacturers face delayed materials.

Food and energy prices can rise.

Inflationary pressure could return just as Trump is struggling to convince voters that his administration is lowering the cost of living.

The economic danger is therefore inseparable from the military campaign.

Iran may be unable to match the United States strike for strike.

It does not need to.

It can use geography, proxy forces, missile attacks and commercial disruption to spread the costs of war.

Hertling described the strategy as “trading space for time.”

Iran may surrender physical positions or absorb damage while extending the conflict long enough for political pressure to build against Washington.

Time can become a weapon.

The longer the war lasts, the more American interceptor stockpiles decline.

The more allies grow nervous.

The more casualties accumulate.

The more voters question the mission.

The more the global economy suffers.

Trump may believe superior firepower guarantees leverage.

Hertling’s warning is that Iran is fighting a different kind of war.

The United States is trying to destroy military capability.

Iran is trying to destroy political patience.

That distinction could explain why tactical American victories have not yet produced strategic success.

U.S. forces can hit transportation hubs, fuel networks and weapons systems with extraordinary precision.

But bombing alone cannot guarantee negotiations on favorable terms.

It can also harden public resistance, strengthen nationalist sentiment and give Iran’s leaders a justification for expanding retaliation.

The administration appears to believe pressure will split Iranian society.

It is possible that the war instead unifies parts of the population against an external attacker.

That outcome would make the political strategy behind the strikes far less effective.

Hertling’s assessment remains expert analysis, not a definitive verdict on the war.

Military conditions can change rapidly.

The United States may possess plans, intelligence or diplomatic initiatives that have not been made public.

Iran’s economic and military position may also be far weaker than it appears.

But the former general’s warning identifies a serious strategic imbalance.

Washington is expending military power without a publicly defined endgame.

Tehran is exploiting geography, alliances, proxy networks and economic pressure.

The United States may dominate the skies.

Iran may still be controlling the clock.

Trump promised strength, speed and decisive victory.

Instead, the ceasefire has faded, American troops have died and two of the world’s most important shipping routes face escalating danger.

If Hertling is right, the greatest threat is not that Iran will defeat the United States in conventional combat.

It is that Tehran will make the war so costly, divided and endless that Washington defeats itself.