In 1980, the US Embassy in Iran was taken by Islamic fundamentalist terrorists. Some of the US students hid out in the Canadian Embassy. What was not known publicly was a Canadian diplomat, with concurrence of the Canadian government, agreed to run an intelligence gathering operation for the USA on the situation in Tehran and at the US Embassy.
The diplomat and the mission's head of security (CF Sgt) and a CIA operative worked together to gather intelligence and it was passed by way of External Affairs (through very few hands, though shown to External Affairs Minister and the PM) to the US.
This intel helped prepare for the failed US rescue attempt (the failure was not the fault of the intelligence, for those who don't know).
The situation in Tehran also had an odd Canadian political dimension. Flora McDonald (Minister of External Affairs for the Clarke Government) was busy conducting affairs related to this situation in Europe when she missed her flight home and missed the close vote that toppled the Clarke government.
http://www.theglobeandmail.com/news/world/canadas-man-in-tehran-was-a-cia-spy/article1441545/
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