Prime Minister Stephen Harper had a one-on-one meeting with Russian President Vladimir Putin on Saturday at the APEC summit.
The prime minister's bilateral meeting with his host came two days after Foreign Affairs Minister John Baird expressed Canada's disapproval of Russia's continued support of Syria's Assad regime with his counterpart Sergey Lavrov.
However, at a photo opportunity before the private meeting, the two men were all smiles, talking about trade and the 40th anniversary of the Canada-USSR hockey summit series. Putin said he met some of the Canadian team members who had travelled to Russia and that he enjoyed talking with them.
Syria was expected to be raised during the private session.
Harper arrived Friday at the 21-nation Asia-Pacific Economic Co-operation gathering, and began his first full day Saturday with a business roundtable before his face-to-face meeting with the Russian president.
Putin kicks off the summit in the Russian city of Vladivostok amid unprecedented popular dissatisfaction with his presidency.
The Russian president faced large protests this spring after his controversial re-election to the presidency. He's also been attacked over last month's two-year prison sentence to members of the punk band Pussy Riot for their anti-Putin "punk prayer" in a Moscow cathedral. The punishment has come to symbolize what many view as Russia's recent backslide on democracy.
Harper and his government have been quiet about the unrest in Russia in the weeks heading into the summit, stressing the economy will be his priority at APEC.