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TORONTO — On March 23, 2016, Kadir Abdul and Samuel Aviles passed through security screening at Toronto’s Pearson airport eight minutes apart and boarded the 5:35 p.m. Air Canada flight to Istanbul.

They landed at Ataturk Airport in the morning and made their way across Turkey, in the path of Abdul’s older brother Malik, who had already crossed into Syria to fight for the Islamic State of Iraq and the Levant.

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The details of the case, revealed here for the first time, offer a rare look at what happens when Canadians suddenly leave home amid concerns they have fallen under the influence of extremist groups.

The incident highlights the difficult choices police, governments and family members face when trying to deal with Canadians who may have become radicalized, as well as the mistakes they sometimes make.

Foreign Affairs Minister Chrystia Freeland said in a speech this week that Canada was “absolutely committed” to fighting terrorism and wanted to become a world leader in counter-radicalization, but the episode shows that gaps exist.