As North Korea has become ever bolder in showing off its ability to create nuclear weapons, writes Anthony Ruggiero, Tehran has been watching closely to see how it can emulate Pyongyang’s success:

North Korea . . . authored the playbook now being used by Iran to fleece the United States and its allies. And if the United States fails to neutralize the North Korean threat, Iran will notice how the United States buckles in the face of nuclear pressure.

The Islamic Republic has already learned a number of damaging lessons from North Korea. First, cheating on nuclear deals is permitted. North Korea cheated twice, and we kept coming back for more. President Bill Clinton announced the 1994 Agreed Framework as a deal that would “freeze and then dismantle its nuclear program,” but Pyongyang violated the agreement when it started a covert uranium-enrichment program.

Washington tried another nuclear deal with the Kim regime, negotiating the 2005 Joint Statement, but North Korea built a nuclear reactor in Syria during the negotiations. The reactor was eventually destroyed by Israel in 2007. Normally that would have ended negotiations, proving that North Korea was not a serious interlocutor. Instead, the Kim regime was rewarded for its nuclear proliferation when the Bush administration removed it from the state-sponsors-of-terrorism list in 2008. . . .

The number of Iranian violations detailed by the UN secretary-general António Guterres in a recent report is stunning. Two Iranian attempts to procure missile components, aircraft parts, and anti-tank missile components from Ukraine were thwarted over a period of just six months. How many others have gotten through? Iran also continues its shipment of arms to the Houthi rebels in Yemen, in violation of two UN Security Council resolutions. . . .

While Iran has learned many lessons from North Korea, Washington should have learned a few, too. The most significant is that flawed, limited nuclear deals do not solve strategic issues.

Israel will likely respond directly against Iran after yesterday’s attack, and has made known that it will calibrate its retaliation based not on the extent of the damage, but on the scale of the attack. The specifics are anyone’s guess, but Edward Luttwak has a suggestion, put forth in an article published just hours before the missile barrage: cut off Tehran’s ability to send money and arms to Shiite Arab militias.

In practice, most of this cash comes from a single source: oil. . . . In other words, the flow of dollars that sustains Israel’s enemies, and which has caused so much trouble to Western interests from the Syrian desert to the Red Sea, emanates almost entirely from the oil loaded onto tankers at the export terminal on Khark Island, a speck of land about 25 kilometers off Iran’s southern coast. Benjamin Netanyahu warned in his recent speech to the UN General Assembly that Israel’s “long arm” can reach them too. Indeed, Khark’s location in the Persian Gulf is relatively close. At 1,516 kilometers from Israel’s main airbase, it’s far closer than the Houthis’ main oil import terminal at Hodeida in Yemen—a place that was destroyed by Israeli jets in July, and attacked again [on Sunday].