It was largely by chance that Israel scored one of its greatest ever intelligence coups in 2007.At the time, Mossad was running surveillance on the director general of the Syrian Atomic Energy Commission, a pudgy, bespectacled bureaucrat named Ibrahim Othman. Othman was visiting Vienna that winter to attend meetings of the U.N.’s nuclear watchdog, the International Atomic Energy Agency (IAEA), and Mossad sought to learn more about his secretive activities. The Israelis hacked the Syrian’s personal computer after he left his hotel for meetings in the Austrian capital.The Israeli government was shocked by what Mossad found on Othman’s laptop. A trove of downloaded photos detailed a box-like building being constructed on the Euphrates River in eastern Syria. Israeli and American spy satellites had detected the mysterious structure during earlier scans of Syria, but derived no special significance to it. Othman’s photos, however, revealed the building, located near a Syrian trading town called Al Kibar, to be a virtual replica of North Korea’s Yongbyon nuclear reactor, a plutonium-producing facility that the U.S. viewed as a virtual bomb-making factory. The facility had no real civilian applications. The Israelis’ concern about the North Korea link was only amplified by a photo Othman stored on his laptop. It showed him standing arm-in-arm with an Asian man whom the Mossad identified as Chon Chibu, a North Korean nuclear scientist who worked at the Yongbyon facility. Chon had previously taken part in disarmament talks with the U.S. and other world powers.While the discovery of the Al Kibar nuclear reactor sparked panic among Israeli and U.S. officials, the fact that North Korea appeared to be taking an active role in providing lethal weapons expertise to one of Israel’s enemies could not have come as a surprise. In fact, while North Korea is not often thought of in the ranks of Israel’s enemies or, for that matter, as a player in Middle Eastern affairs, the so-called Hermit Kingdom in Pyongyang has been actively bolstering states hostile to Israel, and facilitating attacks on the Jewish state, since the 1960s. Despite occasional attempts to broker a truce between the two nations, the Israeli-North Korean relationship has been defined for decades by covert hostility and proxy conflict—a shadow war between the two nations. The pattern continues through the present day in North Korea’s alliance with Iran and Syria.Back in 2007, Israeli Prime Minister Ehud Olmert made it clear to Washington that his government wouldn’t accept Syrian President Bashar Assad developing the capacity to make nuclear weapons. It went against the so-called Begin Doctrine, which held that no Israeli government could allow its regional enemies to possess weapons of mass destruction. This mantra guided Israel’s 1981 attack on the Osirak reactor in Iraq. But concern in Israel was heightened in 2007 by the fact that its intelligence showed the Al Kibar facility was about to go “hot,” meaning uranium fuel would be fed into the reactor. At that point, an Israeli attack risked spreading radioactive contamination across Syria and Iraq, which would fuel wide-spread condemnation of the Jewish state.The George W. Bush administration, meanwhile, faced its own quandary. The U.S. was fighting a growing insurgency in Iraq after overthrowing strongman Saddam Hussein under the faulty pretext that Baghdad was developing weapons of mass destruction. U.S. officials questioned whether Washington could engage in military operations against another Arab state, particularly under the guise of stanching the spread of WMD. U.S. intelligence officials were also struggling to find out how they could have missed Assad’s nascent reactor, while Washington hyped the presence of a nonexistent weapons program in Iraq.Both Israel and the U.S. doubled down in the spring and summer of 2007 to make sure their assessment of Al Kibar was correct. Israel covertly sent commandos into eastern Syria to obtain soil samples from around the facility on the Euphrates. The tests showed positive results for the man-made uranium particles needed for a nuclear program. The Bush administration, meanwhile, scrubbed its intelligence on the movement of North Korean diplomats and trading companies into Syria in the preceding years.The U.S. eventually found the involvement of a troublesome player on the international stage: a company called Namchongang Trading Corp., which was headed by a senior North Korean official named Yun Ho Jin. The U.N. and U.S. sanctioned Yun for being one of Pyongyang’s worst nuclear proliferators. A former North Korean diplomat at the IAEA in Vienna, Yun had used Namchongang in the late 1990s to secretly procure aluminum tubes for his government’s nuclear program from engineering companies in Germany. Yun was seen as a master of using front companies and international smuggling networks to fool rival intelligence agencies. The U.S. believed Yun and his father-in-law, a high-ranking North Korean military officer, played a role in transferring military capabilities to Pakistan, Libya and Myanmar, and including, in some cases, nuclear technologies or materials.Mysteries, however, still abounded about Al Kibar. Both the Israelis and Americans were stumped in trying to find the supporting structures inside Syria needed for a nuclear weapons program. These included a reprocessing facility to harvest the weapons grade plutonium from the reactor and the engineering sites required to convert the fissile material into the metal spheres for a bomb. The U.S. and Israel also questioned who was financing the construction, given Assad’s depleted finances. One theory was that Iran was paying for its close ally’s reactor as a way of owning a satellite nuclear program away from the prying eyes of Western intelligence.The bombing of Al Kibar in 2007 didn’t deter North Korea from continuing to proliferate sophisticated weapon systems to Israel’s enemies, and even, in some cases, its friends in the Middle East. Indeed, concern in Israel over North Korea has only grown in the 12 years since the attack on Syria. Pyongyang’s young leader, Kim Jong Un, has dramatically increased his country’s military capabilities since Donald Trump took office in 2017. The North has tested ballistic missiles that, once perfected, could hit the western U.S., American intelligence officials believe. North Korea has also increased the yield of its nuclear weapons, moving toward what Kim’s government says will be a hydrogen bomb capability. Israel’s security officials say that North Korea’s past actions suggest Kim would have no qualms transferring these capabilities to Israel’s Mideast enemies, particularly for the right price.Concern is now mounting in Jerusalem and Tel Aviv that the Trump administration’s current diplomatic overtures toward North Korea, which are aimed at dismantling its nuclear weapons arsenal, will fail as previous U.S.-led efforts have. Israel could then be forced to again consider taking military action to prevent Pyongyang from distributing its supply of increasingly sophisticated weapons into the Mideast, say current and former Israeli officials.“Americans have made statements that the U.S. would deal with the issue of North Korean missiles, which they never did,” said Eytan Bentsur, a former deputy director of Israel’s Foreign Ministry, who held secret negotiations with North Korea in the early 1990s. “Israel doesn’t have the same timetable in dealing with North Korean threats. “It’s more immediate.”* * *North Korea and Israel, though separated by two oceans and 5,000 miles, have been engaged in low-intensity conflict and high-stakes spy games for more than five decades. For the Jewish state, Pyongyang has presented a remote, yet existential, threat due to its repeated transfer of nuclear and missile technologies to Israel’s sworn enemies in the Middle East. For North Korea, confronting Israel emerged in the 1960s as a central plank in its campaign to fight Western imperialism and U.S.-backed governments. North Korea’s founder, Kim Il Sung, aggressively supported the Palestinian cause, funding and training Arab militants who targeted Israel in terrorist attacks in the 1970s.And yet despite this enmity, North Korea and Israel have also secretly engaged in intermittent diplomacy in recent decades to try and safeguard their national security, at times behind Washington’s back. Israel, on at least two occasions, discussed with North Korean diplomats ways to essentially buy off Pyongyang’s missile exports to the Mideast. The North viewed Israel as a potential economic partner in the wake of the Soviet Union’s collapse, and a conduit to better relations with the U.S. On both occasions, however, the diplomacy died, in part, because of Israel’s inability to act independently from Washington. Some Israeli diplomats have grumbled that their country’s dependence on the U.S. failed to protect them from North Korea’s growing military capabilities and Pyongyang’s exports of sophisticated military technologies to their enemies.North Korea’s strategic threat to Israel goes back to the late 1960s when Kim Il Sung moved to directly insert his military and intelligence services into the Arab-Israeli conflict. Kim, who called Israel an “imperialist satellite” on the Mediterranean, backed Egyptian President Gamal Abdel Nasser and Syrian strongman Hafez al-Assad in their campaigns to reclaim Arab lands lost in the 1967 Six-Day War and push back against Western influence in the Mideast. Pyongyang also staunchly supported Palestinian and left-wing terrorist groups who staged a string of attacks against Israeli targets, both in the Mideast and Europe, during the 1960s and ’70s.In 1972 North Korea trained and financed operatives from the Japanese Red Army, a radical Marxist organization, who attacked Israel’s Lod Airport, killing 26 people and injuring 80 more. The plot played out like a spy novel. The Japanese militants trained with members of the Popular Front for the Liberation of Palestine, or PFLP, in Lebanon’s Bekaa Valley. The PFLP’s commander, George Habash, had traveled to Pyongyang two years earlier to receive guidance from intelligence officials there. The North Koreans paired the PFLP with the Japanese Red Army to help the Palestinians evade Israeli intelligence that was fixated on tracking Arab terrorist threats, according to court documents tied to the Lod case. The North Koreans also provided financing and overall guidance for the plot.The Japanese terrorists in 1972 successfully breached Israeli airport security in ways the Palestinian-Arabs probably couldn’t. The attack quickly deteriorated into a bloodbath. The three Japanese terrorists had sneaked Czech-made machine guns into the airport by hiding them in violin cases. They shot indiscriminately inside the arrival hall and threw grenades. Most of those murdered were Christian pilgrims visiting the Holy Land from Puerto Rico. Two of the Japanese attackers were killed during the shootout. But a third member of the Japanese Red Army, Kozo Okamoto, survived. He spent decades in an Israeli prison before his release, when he returned to Lebanon as part of a prisoner swap.The fallout from the attack has echoed for decades. In 2010, the families of the Puerto Rican victims successfully sued North Korea in a U.S. court for masterminding the attack, winning a $378 million settlement. North Korea never paid.Pyongyang’s military forces moved to directly enter the Arab-Israeli wars in 1973. At the time, Egypt was severing its military ties with the Soviet Union, even as Cairo was gearing up for a surprise attack on Israel. President Anwar Sadat’s expulsion of the Soviet military advisers imperiled Egypt’s ability to operate sophisticated air defenses deployed by Moscow. The Egyptian Air Force was almost totally made up of Russian MiG-21s.Into this breach stepped the North Koreans. Sadat and his army chief, Hosni Mubarak, were impressed by North Korean military capabilities, which were repeatedly on display against South Korea and their U.S. backers. Just a few years earlier, Pyongyang had seized the Pueblo, an American Navy intelligence vessel that had strayed into North Korean waters. North Korea, as a member of the Soviet axis, also understood how to operate all of Egypt’s Soviet-sourced military equipment, including the air defenses and MiG-21s.In June 1973, Sadat formally invited North Korean military advisers to Egypt. According to Chinese press reports, Pyongyang sent nearly 1,500 personnel to help the Egyptians run their Soviet-made surface-to-air missile systems as war with Israel appeared imminent. Pyongyang camouflaged its soldiers as day laborers to avoid detection by the prying eyes of the U.S., Israeli, and South Korean intelligence services. The British researcher Adrian Chan-Wyles translated these Chinese press reports. Pyongyang also sent a North Korean Air Force mission that included 20 experienced combat pilots who had flown sorties against U.S. forces on the Korean Peninsula.As the Yom Kippur War commenced, Israeli military personnel described clashes with North Korean fighters over the Sinai. In October 1973, Israeli Air Force Commander Gen. Benjamin Peled told a press conference that Israeli jets shot down two North Korean-piloted MiGs in dogfights.North Korean pilots also flew with the Syrian Air Force. In the months after the Yom Kippur War formally ended, Israel’s military intelligence still picked up chatter between Syrian jets who were flying intermittent missions against the Jewish state to secure Damascus’ borders. The communications perplexed Israeli analysts, as some of the combatants weren’t speaking Arabic. Rather, they conversed in a language clearly not native to the Middle East or the Syrian Arab Republic.Israeli officers scrambled to gain clarity on the provenance of these mysterious fighter pilots and sent the intercepts to the Pentagon for analysis. The answer they received back from Washington stunned them. They were North Koreans, the Americans said, embedded with the Syrian military. “My initial response was amazement that the North Koreans were there,” Colonel (Ret.) Pesach Malovany, a former Israeli intelligence officer who analyzed the signal intercepts 45 years ago, told me in Tel Aviv. “Our conflict clearly had more than just regional implications.”* * *Following Iran’s Islamic revolution in 1979 that toppled the U.S.-backed shah and installed the theocratic Khomenist regime, North Korea allied itself with the country that would become Israel’s chief regional rival. Kim Il Sung was attracted to the staunch anti-American, anti-imperialist line staked by Tehran’s new Islamist rulers. He quickly deepened diplomatic and economic relations with Iran and sought to expand Pyongyang’s military operations in the Middle East.When Iraq invaded Iran in 1980, a U.S.-led arms embargo made it virtually impossible for Tehran’s new government to secure arms to repel Saddam Hussein’s forces. Kim Il Sung ordered his military to aid the Islamic Republic. North Korean defectors interviewed by this author in Seoul over the past decade said they were dispatched to Iran throughout the 1980s to fortify Iran’s defenses. One senior defector who worked in Pyongyang’s munitions industries said he was sent to Iran by North Korea’s Second Economic Committee with the task of constructing missile batteries on the Iranian island of Kish to help Tehran better control the movement of enemy ships through the Straits of Hormuz.The defector said his main interlocutor was Iran’s elite military unit, the Islamic Revolutionary Guard Corps. The former hydromechanic says camaraderie developed between his 100-man team and the guard, despite their differences in culture and language. He chuckled at how his hard-drinking North Korean team found it challenging to unwind in a country that had banned alcohol. “The Iranians always remember that it was us who came to their defenses when the rest of the world isolated them,” said the defector, in describing why Iranian-North Korean relations flourished and endured.The North Korean-Iranian military alliance continued to advance even after the Iran-Iraq War ended in 1988. It was at this time that the two countries began close cooperation in developing strategic missile systems. This capability allowed Iran to target its Arab adversaries, including Saudi Arabia and the United Arab Emirates. But it would also eventually allow Tehran to target Israel, which Iran’s Islamist leaders viewed as a “cancer” in their region. Yet in the early 1990s, North Korea was facing existential crises on multiple fronts. The collapse of the Soviet Union was drying up Moscow’s financial support for Pyongyang, while also robbing the North of its key export markets in the global communist bloc. Since the end of the Korean War in the 1950s, North Korea had at times outpaced South Korea as a producer of industrial goods. But that dynamic dramatically reversed itself as Seoul emerged as a world leader in the production of electronics, ships and automobiles.North Korea’s founder, Kim Il Sung was in his 80s at the time and suffered from heart problems that would eventually claim his life. There was great uncertainty in Pyongyang about his chosen successor, eldest son Kim Jong Il, and his ability to lead the country at such a challenging time. The younger Kim had a reputation of being a womanizer and drunkard who preferred making movies to statecraft.It was in this context of instability at the top that North Korea, in 1992, made a covert overture to Israel. The North was seeking ways to address its economic malaise and viewed the Jewish state as a potential partner in rehabilitating its industry. The North’s leaders also may have believed that Israel, and its powerful political lobby in the U.S., could be a conduit for better ties with the U.S. at a time when Pyongyang’s alliance with Moscow was in question.The North’s initial outreach to the Israelis came in September 1992 through a Korean American businessman. The businessman contacted the Israelis through a relative of Eytan Bentsur, the deputy director general of Israel’s Foreign Ministry, who was visiting Washington at the time for negotiations with the Palestinians. An initial meeting was set up in the diamond district of mid-Manhattan. Pyongyang’s initial request was simple: It sought a $30 million Israeli investment in a gold mine destroyed by the U.S. Air Force during the Korean War, as well as technical assistance to rehabilitate it. Successful cooperation on this project in central Unsan Province, the North hoped, could open up other paths for economic cooperation between the two countries.Bentsur said in interviews that he was intrigued by the offer because of Israel’s growing concern about North Korea transferring ballistic missile technology to its regional adversaries. A strengthened relationship, he argued, could potentially stanch the flow of this weaponry and relieve what was emerging as the existential threat posed by the missiles systems of Iran, Syria, and Libya to Israel. A better relationship with Pyongyang, Bentsur argued, would also be in the interest of Washington, which still had tens of thousands of soldiers stationed on the Korean Peninsula to face down the North Korean threat. “The USSR was being dismantled. And starvation was taking root in North Korea,” Bentsur told me at a coffee shop in Tel Aviv. “They were looking for help.”Bentsur proceeded in 1992 and 1993 to hold a series of negotiations with North Korea, both in Beijing and Pyongyang. The diplomat included experts in mining and minerals from Israeli universities to study the feasibility of rehabilitating the North Korean mine. And the Israelis started to broach the idea of Pyongyang’s missile exports during the discussions. Bentsur said his team made clear to their interlocutors that any economic assistance from Israel would have to include Pyongyang ceasing its Mideast weapons trade. North Korea sought a larger fund of $1 billion for investments in the country.In a November 1992 visit, Bentsur was put up at a state guesthouse where the chairman of the Palestinian Liberation Organization, Yasser Arafat, once stayed. “We were kept in fantastic luxury,” Bentsur said of his sleeping in the same room as the Arab revolutionary. As the talks progressed from solely focusing on the mine to greater economic engagement, North Korea specifically stated that it expected to be compensated financially for ceasing its missile sales to the Mideast. Pyongyang estimated that it earned hundreds of millions of dollars from the trade per year.Ultimately, Bentsur and his team believed they had the parameters of an agreement with the North. Israel would help with the mine, establish the $1 billion fund and seek ways to address North Korea’s energy shortages. Pyongyang, in turn, would cease its missile exports to Israel’s enemies. “North Korea was ready to let Israel open a diplomatic mission. They wanted Peres to visit Pyongyang,” Bentsur told me, referring to Israel’s then foreign minister, Shimon Peres. “They agreed to let Israelis monitor their ports.”But the deal never took hold. Unbeknownst to Bentsur, the North Koreans had pursued a separate channel of diplomacy with Israel through Mossad, the country’s famed spy service. Mossad’s deputy director at the time, Ephraim Halevy, was concurrently holding negotiations with Pyongyang focused on a 10-year plan for energy assistance. The two men traveled separately to Pyongyang in November of 1992 for discussions. And they were surprised to find one another on the same flight back from North Korea to China on Pyongyang’s state airline, Air Koryo. The North had purposefully kept the two men in the dark about the twin diplomatic channels.Halevy didn’t share Bentsur’s optimism about engaging with North Korea. The British-born spy thought the North Koreans were trying to manipulate Israel by using economic trade as a way to diminish the U.S.’ leverage over its historic enemy. Halevy informed the Central Intelligence Agency about the secret talks and got word from Washington that the Clinton administration didn’t support the initiative. Foreign Minister Peres would get the same message from his American counterpart, Warren Christopher, in early 1993. “We couldn’t step into North Korea on our own without any recourse to how it would play in Washington,” Halevy told me in Tel Aviv. “We weren’t a player in Asia.”Just months later, an international crisis erupted when United Nations nuclear inspectors discovered that North Korea had been diverting plutonium from its Yongbyon reactor, potentially for weapons use. The Clinton administration entered into negotiations with Kim Il Sung’s regime, and the two sides eventually reached a deal not dissimilar to the one Bentsur and Halevy pursued. The U.S. agreed to provide energy assistance to North Korea, in the form of oil shipments and light water reactors, in return for North Korea shuttering the Yongbyon facility. But the deal, known as the Agreed Framework, never addressed North Korea’s missile exports to the Middle East. And Pyongyang would continue to conduct covert nuclear work behind the backs of the U.S. and U.N. Indeed, North Korea would ultimately master two technologies for building nuclear bombs: One involved harvesting the plutonium produced by the Yongbyon reactor; the second used centrifuge machines to produce weapons-grade uranium.In 1999, Israeli diplomats secretly entertained another offer from North Korea to cease its missile exports. This time, the North reached out to the Jewish state through diplomats based in Stockholm. Pyongyang said it would charge Israel $1 billion to cease exporting its more advanced missile systems to Syria and Iran. Israel responded that it couldn’t make such cash payments to the North behind the back of the Americans.* * *Despite these encounters with North Korea, Israeli officials say they never had particularly great intelligence on the country’s global activities. Pyongyang was largely viewed as an American problem, regardless of the threat the Kim regime posed to vital Israeli security interests. Still, rumors swirled in South Korea at times that Mossad was active in running sabotage operations against the North. In the spring of 2004, a massive explosion struck a North Korean train that was transiting near the Chinese border, killing more than 50 people. Some news reports in Asia alleged that Syrian military personnel were among the dead. This stoked speculation that Israeli spies targeted the train to block Pyongyang’s missile exports. I was unable to confirm such an operation took place, despite extensive reporting trips to Seoul and Israel.The North Korean-built nuclear reactor in Syria posed a threat that Israel could not ignore even after President Bush decided in the summer of 2007 against using America’s military to destroy the facility. The inability of U.S. intelligence to answer the outstanding questions about Syria’s nuclear capacity was one important reason for Bush. But he also told his aides that he couldn’t risk another regional Mideast war in the waning months of his second term. He suggested to Olmert that the U.S. report Syria to the IAEA for violating international nonproliferation statutes and try to remove Damascus’ threat diplomatically. The Bush administration was concurrently pursuing talks with North Korea aimed at dismantling its growing nuclear weapons arsenal. Secretary of State Condoleezza Rice believed a strike on Al Kibar could disrupt that process.Olmert accepted Bush’s rationale, but made clear Israel was preparing to act alone. His aides believed any diplomatic track involving the IAEA would result in a prolonged negotiation that risked legitimizing Syria’s nuclear program. They had watched a similar dynamic play out after Iran was caught secretly building nuclear sites in 2002.On the evening of Sept. 5, 2007, eight Israeli aircraft secretly took off from two air force bases in the Negev desert and flew north over the Mediterranean and then east into Turkish air space before entering Syria. The jets completely destroyed the Al Kibar facility before returning safely to Israel. Olmert placed a blackout on the Israeli media reporting on the attack. President Assad also kept quiet, embarrassed by the strike’s exposure of his country’s slack air defenses. Only North Korea publicly condemned the operation. U.S. officials said a number of North Korean workers died during the bombing of Al Kibar.Many Israeli and American officials, however, remain concerned about the lessons learned from the episode. Olmert was relieved that Assad didn’t respond militarily to the strike and potentially stoke a regional war. But neither Syria nor North Korea ever paid any real diplomatic or financial cost for their blatant acts of nuclear proliferation. Indeed, the Bush administration continued its pursuit of a nuclear agreement with Pyongyang and removed the North from its list of state sponsors of terrorism in 2008. Even then, Bush never got the disarmament pact he sought. North Korea backed out of the talks in the waning months of his presidency and proceeded to dramatically increase its production of atomic bombs and long-range missiles. Syria and North Korea, meanwhile, always denied they’d cooperated to build the reactor on the Euphrates River.The lesson for North Korea was that it could proliferate, in the Middle East and elsewhere, and get away with it. “I believe our approach towards North Korea at the end of Bush’s term set an incredibly dangerous precedent,” said Elliott Abrams, Bush’s top Mideast advisor at the White House who took part in the discussions on Al Kibar. “We’re paying for it now.”* * *In Syria, North Korea has rushed to help President Assad win the brutal civil war waged since 2011. While Russia, Iran, and the Lebanese militia Hezbollah have been Assad’s biggest allies in the brutal conflict, North Korea has also been fused into the Syrian dictator’s war machine, according to U.S., U.N., and Arab officials.Production of the chemical weapons Assad has used to gas thousands of Syrians is one key role North Korea has played in the civil war. U.N. inspectors detailed in a confidential report last year how North Korean trading companies smuggled tons of industrial equipment into Syria to build a new chemical weapons facility in collaboration with Syria’s Scientific Studies and Research Center. The SSRC oversees Assad’s chemical weapons production. These shipments were tracked by several U.N. member states and included acid-resistant tiles, stainless steel pipes, and other materials associated with chemical weapons production. The U.N., in the report, identified 40 previously undisclosed North Korean shipments to the SSRC from 2012 to 2017.The U.N. also detailed North Korea’s deployment of its engineers at Syrian military bases active in the civil war. These personnel helped Damascus manage its chemical weapons and missile plants at bases in Hama, Adra, and Barzah, according to the U.N. Soldiers from Iran’s elite military unit, the Revolutionary Guard, and Hezbollah have also been active in these areas and targeted by dozens of Israeli airstrikes during the war. Israel is concerned that the IRGC and Hezbollah are seeking to establish permanent bases inside Syria to launch cross-border attacks into the Jewish state. This raises the possibility that Israel may again be attacking North Korean personnel inside Syria, as it reportedly did at Al Kibar in 2007.Syria has lauded North Korea for its military alliance and diplomatic support. In 2015, the Assad regime inaugurated Kim Il Sung Park in a Damascus suburb. It sits adjacent to a 1-kilometer street also named after North Korea’s founder. The ceremony was held to mark the anniversary of the establishment of North Korea’s ruling Workers’ Party. Kim Il Sung was an “historic ruler and leader, famous for his struggle to liberate and build his country,” Deputy Foreign Minister Faisal Mikdad said at the ceremony, according to Syrian state media. “For this reason, he deserves to be honored in Syria.”Egypt has also continued to be a buyer of North Korean weapons in recent years, despite Cairo’s military alliance with the U.S. and diplomatic relations with Israel. These arms purchases have stoked tensions between the Trump administration and the Egyptian government. The U.S. has been trying to starve Pyongyang of its revenues from military sales in a so far unsuccessful bid to force Kim Jong Un to give up his nuclear arsenal. The Trump administration withheld nearly $300 million in military aid from Egypt in 2017 in order to force President Abdel-Fattah el-Sissi’s government to cut off these transactions.Egypt’s purchasing of North Korean weapons speaks to the depths of the relationship Cairo and Pyongyang forged back in the 1950s, according to U.S. and Arab officials. It also illustrates how Pyongyang has transformed itself into a major supplier of low-cost guns, munitions, and missiles to developing countries in Asia, Africa, and the Middle East. Pyongyang mastered the use of sophisticated front companies, smuggling routes, and false flagged vessels to work around U.S. and U.N. sanctions.The U.S. was alarmed in the summer of 2016 when a Cambodian flagged merchant ship, the Jie Shun, left from the North Korean port of Haeju for the Suez Canal. The ship contained a 23-man North Korean crew and cargo shrouded under heavy tarps. Egyptian authorities eventually boarded the vessel before it transited the canal, after being tipped off by U.S. intelligence agencies who were concerned about the nature of cargo. Under the tarp, the Egyptians found coal that sat atop 30,000 North Korean rocket-propelled grenades. A U.N. report concluded that the Jie Shun marked the largest seizure of North Korean munitions since international sanctions were enacted against Pyongyang in the 1950s. The weapons were valued at $23 million.* * *No country in the Middle East has had deeper cooperation with Pyongyang in missile development than Iran, according to U.S. and Israeli officials. Tehran’s nuclear program is by far the most advanced in the region, besides Israel’s, and the best positioned to benefit from North Korea’s technological advances.U.S. and South Korean intelligence have been tracking the movements of Iranian and North Korean military officers and scientists between their countries in recent years. One South Korean official said they’ve documented hundreds of North Koreans traveling to Tehran using a range of real and forged passports. Many transited into Tehran on flights that originated from Qatar’s international airport.The Obama administration announced in 2016 that American intelligence agencies found that Iranian technicians from Tehran’s defense industry decamped in North Korea to jointly develop an 80-ton rocket booster for ballistic missiles. Pyongyang’s Korea Mining Development Trading Corp. also was caught shipping key components for liquid propellant ballistic missiles and space launch vehicles to Iran. This included valves, electronics, and measuring equipment.The West’s concern about North Korean-Iranian military collaboration spiked on Sept. 22, 2017, during the Revolutionary Guard’s annual Sacred Defense Week. The event includes a parade that commemorates the 1980-88 Iran-Iraq War in which hundreds of thousands of Iranians died repelling Saddam Hussein’s forces from their country. Banners hung at the event included the mantras, “Death to America” and “Death to Israel,” written in three languages.Transported down a major Tehran thoroughfare that day was a new medium-range, Iranian ballistic missile, called the Khorramshahr after the Iranian city where a crucial battle of the Iran-Iraq War took place. The missile is estimated to have a flight range of between 2,000 and 3,500 kilometers, depending upon the weight of its payload. At this distance, Tehran could target Israel, the Persian Gulf and a number of countries in the North Atlantic Treaty Organization.American and Israeli intelligence officials who analyzed photos of the Khorramshahr quickly noticed its similarities in size, construction and flight dimensions to a North Korean missile called the Hwasong-10, or Musudan. Pyongyang developed the Musudan by reengineering missile technologies it acquired from the former Soviet Union in the 1990s. North Korea is believed to have sold the missile technologies for the Musudan to Iran in recent decades. But both countries have had difficulties mastering its physics and engineering, according to U.S. and Israeli officials.Despite faltering progress in deploying the Musudan, “there is, nonetheless, no doubt that the Khorramshahr missile constitutes a potential threat to Europe,” wrote Uzi Rubin, a renowned missile expert at the Begin-Sadat Center for Strategic Studies in Tel Aviv. “If and when Iran develops a nuclear weapon, it will not be complicated to fit a lighter weight nuclear warhead on the Khorramshahr and thereby threaten Berlin, Brussels, Paris and Rome.”North Korea’s and Iran’s missile programs complement each other in a number of important ways, say Israeli intelligence analysts who track them. Pyongyang has a better mastery of the electronics used in the navigation systems of the projectiles, while Tehran is seen as having a better grasp of the solid-fuel propellants used to ignite them.In recent months, Israeli analysts have theorized that North Korea and Iran may be sequencing their tests. They note, for example, that North Korea tested an intercontinental ballistic missile, called the Hwasong-14, on July 4 of 2017. The Iranians then tested a space-launch vehicle, called the Simorgh, just a few weeks later on July 27. The rockets share a number of important properties. “Is it coincidental? Maybe. But it seems like they’re learning from each other,” said an Israeli intelligence analyst in Jerusalem. “It seems to be a two-way street.”To date, Israeli, American, and IAEA officials say they haven’t seen hard evidence that North Korea and Iran are directly sharing nuclear technologies or materials, in ways similar to how Pyongyang transferred them to Syria and Libya. But the regular exchanges of Iranian and North Korean defense officials and scientists are being heavily scrutinized.North Korea and Iran signed a formal scientific cooperation agreement in the fall of 2012 when Pyongyang’s No. 2 political leader, Kim Yong Nam, visited Tehran. The pact doesn’t specify nuclear collaboration, but its language is eerily similar to one Pyongyang signed with Syria in 2002, just months before the construction of the Al Kibar reactor is believed to have started. The head of the Atomic Energy Organization of Iran at the time, Fereydoun Abbasi-Davani, attended the signing of the agreement. And it called for the establishment of joint laboratories, exchanges of North Korean and Iranian scientists, and technology transfers in the areas of energy and information technology.“The Islamic Republic of Iran and North Korea have common enemies since the arrogant powers can’t bear independent governments,” Supreme Leader Ayatollah Ali Khamenei told Kim Yong Nam during his visit, according to the official Fars news agency.American and Israeli intelligence officials say they’ve seen evidence that Iranian military officers and technicians have attended some of the six nuclear tests Pyongyang has conducted since 2006. They say they’ve also seen them attending North Korean military parades and missile tests. A particular focus has been placed on a 2013 North Korean test that’s believed to have involved a uranium bomb. Iranian opposition groups have said the putative father of Iran’s nuclear weapons program, a Revolutionary Guard General named Mohsen Fakhrizadeh, was in attendance. American and Israeli intelligence officials say they haven’t ruled out this possibility.“Are they cooperating in the nuclear field? That’s an open question,” concluded an Israeli intelligence analyst.***Like this article? Sign up for our Daily Digest to get Tablet magazine’s new content in your inbox each morning.