A suspected US drone strike on Saturday morning killed an Ahrar al-Sham commander in Idlib, the first western strike targeting the group in almost three years.
Abu Hani al-Masri, an Egyptian fighter who had previously fought with al-Qaeda in Afghanistan, Somalia and Chechnya, was reportedly killed in the targeted strike.
A spokesperson for the Pentagon was not able to immediately confirm or deny the US' involvement.
Previous coalition strikes in Idlib province have mainly targeted militants from Jabhat Fateh al-Sham, formally known as al-Nusra Front - an al-Qaeda affiliate.
Masri was killed ten kilometres away from a major border-crossing with Turkey, between the towns of Sarmada and Batabo.
The US does not currently list Ahrar al-Sham as an extremist organisation, however today's strike has raised questions among many Islamists militants over whether that has changed under the new administration of Donald Trump.
Sheikh Muslih al-Alyani, a jihadist cleric who previously joined al-Qaeda, said Masri's death signified that Ahrar al-Sham could now be considered an extremist organisation by Washington.
Large numbers of Syrian rebels joined Ahrar al-Sham last week after Jabhat Fateh al-Sham launched a campaign against rebel fighters in Idlib province.
Although Ahrar al-Sham holds a militant Islamist world-view, it has not expressed the same intentions of world conquest as Jabhat Fateh al-Sham or Daesh.
Masri spent around ten years in an Egyptian prison for being a member of al-Qaeda, before being pardoned by President Mohamed Morsi in 2012.
Lebanon's Ad-Diyyar reported in 2002 that Masri was the al-Qaeda commander responsible for defending Kandahar airport with the Taliban.
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