Following the fall of the Assad regime in Syria, President Donald Trump has taken an unusually open approach toward Damascus, seeking to usher in a new era of stability and regional integration. But that strategy is beginning to face significant tests from jihadist elements embedded within Syrian President Ahmad al-Sharaa’s own military ranks.

In his second term, Trump has made unprecedented moves to normalize relations with Damascus and promote a new political order in Syria following the fall of the Assad regime last year. During a Middle East visit in May, Trump became the first American president in 25 years to meet with a Syrian leader and announced the lifting of U.S. sanctions on Syria that had been in place for more than a decade. On Nov. 10, Trump hosted al-Sharaa at the White House in a historic visit, during which Syria formally joined the U.S.-led anti-ISIS coalition. The administration has also sought to broker a security agreement between Syria and Israel.

Despite those efforts, experts warn that Trump’s push for stabilization is increasingly being challenged by the incorporation of jihadist-aligned figures into Syria’s emerging military and security apparatus.

“What my colleagues and I have been warning this entire year is that al-Sharaa was putting his jihadist allies into the new Syrian military without apparent measures to prevent bad things from happening,” said David Adesnik, vice president of research at the Foundation for Defense of Democracies, who added that those with jihadist beliefs were integrated in “large groups.”

Those concerns were underscored earlier this month, when two U.S. soldiers and one civilian contractor were killed in Syria in an attack claimed by the Islamic State (ISIS) — the first U.S. casualties in the country since Assad’s fall in December 2024. Reports indicated the assailant was a lone gunman who had previously served in Syria’s Internal Security service and had extremist leanings.  

“The ISIS attack that killed U.S. service members and a civilian should be a wakeup call that the terrorist group is still a threat, and will seize opportunities to reconstitute,” said Dana Stroul, director of research at The Washington Institute for Near East Policy. “So far, the Trump team has tested al-Sharaa’s forces by asking them to go after ISIS threats and the record is fairly positive. But the ‘Defeat ISIS mission’ is not complete.”

While ISIS remains active in parts of Syria — particularly in the country’s northeast, where U.S. forces have long maintained a presence — some experts told Jewish Insider that jihadist figures aligned with al-Sharaa in the new Syrian military are the more immediate challenge to stabilization efforts.

John Hannah, a senior fellow at the Jewish Institute for National Security of America, said al-Sharaa’s decision to formally align with the U.S.-led anti-ISIS coalition has not only provoked ISIS, but also energized jihadist elements within Syria’s ranks.

“ISIS has been relatively quiet since the collapse of the Assad regime. That’s clearly changed over the past couple of months,” Hannah said. “That decision to sign on with a posse led by the Americans against fellow Muslims served as a major provocation — not just to ISIS, but to the broader jihadist community, including fighters now inside Syria’s new formal security structures.”

“There have been deep feuds among jihadis, and al-Sharaa was on one side in a feud against the Islamic State,” said David Adesnik, vice president of research at the Foundation for Defense of Democracies. “Al-Sharaa is also invested very heavily in a better relationship with the United States. The last thing he needs is a guy in his own ranks killing Americans and potentially throwing all of this off.”

In a Truth Social post, Trump vowed “very serious retaliation” to the attack, writing that the Syrian president “is extremely angry and disturbed by this attack.” The U.S. conducted strikes on multiple ISIS targets in Syria last Friday.

Adesnik said Trump’s comments likely accurately “represent al-Sharaa’s views,” noting that ISIS has long been a rival to al-Sharaa within the jihadist ecosystem.

“There have been deep feuds among jihadis, and al-Sharaa was on one side in a feud against the Islamic State,” Adesnik said. “Al-Sharaa is also invested very heavily in a better relationship with the United States. The last thing he needs is a guy in his own ranks killing Americans and potentially throwing all of this off.”

Days after the attack, Trump signed an executive order barring Syrian nationals from entering the United States. The order “adds full restrictions and entry limitations” on Syria “based on recent analysis.”

Stroul said that while this is “not a significant change in U.S. policy toward Syria,” it will be “received poorly by Syrians.”

“On a positive note, the EO clearly acknowledged the work of the one-year-old government in Damascus to address its security challenges, in coordination with the U.S.,” said Stroul. “This suggests that once the U.S. has confidence in the security procedures of Damascus, it could reverse this decision.”

But signs of ideological extremism within Syria’s new military have continued to surface. Shortly before the attack, video surfaced of what appeared to be a group of Syrian army soldiers chanting a jihadist declaration of war against Israel during a military parade in Damascus.

“It should have been obvious quite a while back that there were large groups within the Syrian military that had precisely this belief,” Adesnik said. “It goes back to the fact that [Syria’s new leadership] has integrated a large number of al-Sharaa’s jihadi forces, or aligned jihadi forces, into the military. Being deeply anti-Israel to the point of supporting Hamas is sort of par for the course if you’re a jihadist.”

Adesnik added that such views are consistent with al-Sharaa’s past rhetoric on Israel. Pro-Israel critics of al-Sharaa have pointed to the Syrian leader’s past ties to Al-Qaida, a U.S.-designated Foreign Terrorist Organization and group he joined following the 2003 U.S. invasion of Iraq. While operating for the group as a foot soldier, al-Sharaa was captured by U.S. military forces and imprisoned. He later founded one of the terror group’s Syrian branches.

U.S. officials have played down concerns about Syrian intentions toward Israel. Tom Barrack, the U.S. ambassador to Turkey and special envoy to Syria, told reporters last week that Damascus is not interested in aggression against the Jewish state. But Israeli officials have taken a more pessimistic view, with Israeli Diaspora Affairs Minister Amichai Chikli writing on X that war with Syria is “inevitable.”

“The SDF have been America’s most reliable and effective partner in fighting ISIS for more than a decade,” John Hannah, a senior fellow at the Jewish Institute for National Security of America, said. “The logic of incorporating those SDF units wholesale into al-Sharaa’s army and then unleashing them with U.S. backing on the ungoverned spaces of Syria’s central desert where ISIS has found real sanctuary is compelling.”

The White House has aimed to broker a security agreement between Damascus and Jerusalem, in which the Jewish state would relinquish territory it holds within Syria. However, Israel has differed on this approach due to security concerns and a deep distrust of the leadership in Damascus. The two sides reportedly remain far apart on any potential agreement. 

The U.S. currently maintains roughly 1,000 troops in Syria, supported by U.S. air power, and continues to work with the Kurdish-led Syrian Democratic Forces (SDF), a longtime American partner that has played a central role in combating ISIS. Hannah argued that integrating the SDF into Syria’s new security structures could help counteract jihadist and ISIS influence in the country.

“The SDF have been America’s most reliable and effective partner in fighting ISIS for more than a decade,” Hannah said. “The logic of incorporating those SDF units wholesale into al-Sharaa’s army and then unleashing them with U.S. backing on the ungoverned spaces of Syria’s central desert where ISIS has found real sanctuary is compelling.”

Adesnik echoed that view, calling SDF integration “definitely a good idea,” while cautioning that progress is likely to be slow.

“There was an interim agreement in March, but the odds of that happening in the next few weeks are very low,” Adesnik said. “As long as it doesn’t go completely off the rails, they’ll probably kick the can down the road.”

Despite the challenges to stabilization, Stroul said that U.S. policy toward Syria will likely “remain consistent,” and that she expects the Trump administration to continue embracing the new government in Damascus and al-Sharaa’s leadership. 

“President Trump is about to sign into law the bipartisan NDAA which lifts the sweeping Caesar sanctions against Syria — this was requested by the Trump team and the al-Sharaa government to Congress,” said Stroul. “This is a critical step in sanctions relief that will allow foreign investment to flow into Syria without fear of U.S. punitive action, and is a major signal of support for the post-Assad Syria.”

One year after the fall of the Assad regime in Syria, policymakers and officials in the United States and Israel remain increasingly divided over how to confront the changing landscape in Damascus.

Following the fall of Bashar al-Assad in December 2024, the IDF moved into a U.N. buffer zone inside southern Syria to protect Israel’s northern border as Damascus’ military and political landscape shifted. A year later, against Damascus’ wishes, Israel still controls the 155-square-mile area and has proceeded to carry out arrests of terror suspects, while also seizing weapons and conducting targeted airstrikes. 

These actions have collided with President Donald Trump’s push to broker a security agreement and end hostilities between the two countries, which the president and some experts see as a key part of stabilizing Syria — and, ultimately, the region. The Trump administration has often sided with Damascus in recent disputes, warning that Israel’s strikes are undermining efforts to reach an agreement, which the White House also views as a path to normalization. 

Israeli Prime Minister Benjamin Netanyahu maintains that any agreement must require Syria to accept the demilitarization of territory stretching from southern Damascus to the Israeli border. However, Syrian President Ahmad al-Sharaa has rejected this condition, arguing that it would create a dangerous security vacuum in southern Syria. 

Critics of al-Sharaa and some in the pro-Israel community have remained wary of relinquishing the area to the Syrian government given al-Sharaa’s past ties to Al-Qaida, a U.S.-designated Foreign Terrorist Organization that he joined following the 2003 U.S. invasion of Iraq. While operating for the group as a foot soldier, al-Sharaa was captured by U.S. military forces and imprisoned, and he later founded one of the terror group’s Syrian branches. 

“In [Israel’s] perspective, the problem is mistrust as well as hard security indicators,” Ahmad Sharawi, a research analyst at the Foundation for Defense of Democracies, told Jewish Insider. “Southern Syria is awash with weapons, weapon trafficking routes and Iran-backed networks. At the same time, Israel is being asked to make concessions to a government led by a former Al-Qaida emir whose coalition still includes figures that praised the Oct.7 attacks and openly endorse armed resistance against Israel.”  

Jonathan Ruhe, a fellow at the Jewish Institute for National Security of America, explained that Israel is concerned that should a deal be made, it could allow for “potentially hostile forces to encroach anywhere near the border.” In a conversation with the Hudson Institute last month, Caroline Glick, international affairs advisor to Netanyahu, said keeping threats away from Israel’s borders has become an instrumental part of the Israeli government’s foreign policy in the aftermath of the Oct. 7, 2023, terrorist attacks. 

“Defense is simply not an option for such a small country, and thus the security of each and every border matters more for Israel than most any other country,” said Ruhe. “To be viable for Israel, a deal would have to demilitarize southwest Syria and probably include real prohibitions on Turkish military presence in Syria. It also likely would have to permit Israel to use Syria as an air corridor to Tehran, or at least not openly prohibit this.”

Reflecting the views of those urging an accommodation towards the new Syrian government, Barbara Leaf, assistant secretary of state for Near Eastern affairs under the Biden administration, maintained that Israel has nothing to worry about with a normalized al-Sharaa government.  

Participating on a panel at the Middle East Institute on Wednesday, Leaf refrained from addressing Israel’s security concerns, instead arguing that Syria holds no hostile posture towards the Jewish state and that Israel’s actions are prohibiting an agreement. She pushed for the U.S. to exert more pressure. 

“There’s no other recourse but for the White House to come down very hard and definitively on the Israeli government to stop the bombing and to start making plans to pull back from that border and get serious and finish this set of discussions,” said Leaf. 

Sharawi suggested that Israel remains hesitant and has taken a “far more pessimistic view of Syria’s short-term trajectory. 

“Even if al-Sharaa himself is signaling restraint, Israeli decision-makers are deeply skeptical that his control is durable or that he would retain power long enough to enforce any agreement,” said Sharawi. 

Last month, Trump administration officials indicated that a security deal was “99% done,” with hopes that Trump’s Oval Office meeting with al-Sharaa in November could help push the agreement over the line. But talks continue to stall. 

Gideon Sa’ar, Israel’s foreign minister, said on Wednesday that the gap between the two sides has grown, as the Syrians have added new demands.

Ruhe said it may also be tricky for the White House to fast-track an agreement as Trump could have less room to exert pressure on Israel.

“Partly it’s a question of how much pressure Trump can still apply to Israel, since he already leaned hard on Netanyahu to agree to the Gaza ceasefire,” said Ruhe. “Any foreseeable deal would be a narrow nonaggression pact, not Syria joining the Abraham Accords as Trump may wish.”