Canada carried out its first air strikes in Syria on Wednesday the military said, expanding Ottawa's contribution to the US-led coalition against Islamic State, after parliament approved a larger role in the conflict.
Two F-18s using precision-guided munitions struck a IS position near the Syrian city of Raqqa, before safely returning to base, the military announced.
The strike near Raqqa, an IS stronghold, was carried out with a group of 10 aircraft, including six US planes.
Canadian strikes had been limited to Iraqi territory, but at the end of March Canadian lawmakers narrowly passed a measure to allow the country's aircraft to target IS targets in Syria.
Opposition lawmakers argued Canada should not deepen its involvement in the long-running and complex war.
Canada first joined the anti-IS coalition in November and it has also deployed about 70 special forces troops to train Kurds to fight IS in northern Iraq.
Despite a sustained air campaign and ground advances in Iraq, the radical group still holds large swaths of territory straddling Syria and Iraq.