The government of Canadian Prime Minister Justin Trudeau learned a valuable lesson Sunday afternoon about how far it is advisable to push the Saudi Arabian government. While critics of President Trump point (often with good justification) to the sometimes boorish and heavy-handed way he deals with foreign leaders, Trudeau, for all his apparent charm, hasn’t been able to stop his government from stepping on its own toes.

Last week, Saudi Arabia arrested two activists: Samar Badawi and Nassima al-Sadah. Badawi’s brother, Raif Badawi, is a Saudi blogger who the government jailed in 2012 for “insulting Islam through electronic channels.”

Canada’s foreign minister, Cynthia Freeland, tweeted Thursday in French and English, “Very alarmed to learn that Samar Badawi, Raif Badawi’s sister, has been imprisoned in Saudi Arabia. Canada stands together with the Badawi family in this difficult time, and we continue to strongly call for the release of both Raif and Samar Badawi.”

While I’m a supporter of the universal right to freedom of speech and expression, there is a time and a place for everything. Even with the crown prince, Mohammed bin Salman, doing his best to rehabilitate the fundamentalist country’s image, there is only so far one should attempt to push the Saudi government. Canada just pushed past that point.

A convoluted situation

Last month, Raif Badawi’s wife and children gained Canadian citizenship. This move was clearly designed to push the Saudi government, in addition to giving Canada the justification it needed to launch a verbal broadside at Riyadh.

As you can imagine, this did not sit well with the Saudi government.

In an official statement, the Saudi Press Agency said, “the Canadian statement is a blatant interference in the Kingdom’s domestic affairs, against basic international norms and all international protocols. It is a major, unacceptable affront to the Kingdom’s laws and judicial process, as well as a violation of the Kingdom’s sovereignty.”

In response, the Saudi government recalled its ambassador from Ottawa and expelled Canada’s ambassador, giving him 24 hours to leave the country.

The Kingdom also announced it was halting any new investments in Canadian ventures. This is no small move. The Saudi Public Investment Fund (PIF) is a “sovereign wealth fund” that as of a year ago had more than $220 billion in assets. PIF invests like any other private equity or venture capital fund would: It uses the Saudi government’s money to provide working capital for companies in an attempt to turn a profit.

In addition to a host of Saudi companies, the PIF has taken positions in global shipping company Hapag-Lloyd, Japan’s Softbank Vision Fund, and Wall Street investing powerhouse Blackstone. It also provided the single-largest infusion of capital—$3.5 billion—to the American ride-sharing tech giant Uber. This is not a fund that any head of government would want to have freezing its activity in his country.

Predictably, the Canadian dollar’s value dropped 0.3 percent, erasing recent gains.

Latest gaffe for Trudeau

The Canadian move is just the latest misstep for Trudeau. To cite one example, back in February, Trudeau and his wife toured India. During their trip, the couple sported traditional wedding attire in an attempt to look appreciative of Indian culture (it backfired, with one at least one Indian politician tweeting his displeasure). To make things work, the prime minister awkwardly invited a Sikh activist, Jaspal Atwal, to a reception.

India is very sensitive about the Sikh separatist movement. For his part, Atwal was convicted in 1986 of participating, along with three others, in an attempted assassination of an Indian government official, Malkiat Singh Sidhu, in Vancouver. Atwal is still a Canadian citizen, and has supported many politicians in Trudeau’s Liberal Party. While that certainly gains him some clout in Canadian political circles, it does nothing for him in India.

Even though the invitation was cancelled, inviting Atwal to an official function during a trip to India would be like Donald Trump inviting Bernadette Sands McKevitt—sister of Irish Republican Army volunteer Bobby Sands who died on hunger strike in 1981, and husband of Michael McKevitt, founder of the anti-Good Friday Agreement splinter group “Real IRA”—to tea while visiting London. It’s just not a good idea.

An obscure back-bench member of the Canadian parliament took responsibility to inviting Atwal, but the incident points to a wider Liberal Party habit of pushing forward with its progressive ideals without giving the slightest thought to how other governments who don’t share that progressive outlook might interpret those rules.

President Donald Trump is learning (even if only privately) that he can’t get by on the international stage with only bluster. Trudeau, one hopes, is learning that charm, good looks, and the mastery of the sound bite might win elections in Canada, but they aren’t necessarily winning Canada friends around the world.

Trump and U.S. Ambassador to the United Nations can get away with criticizing countries like Iran and Syria on Twitter because there’s nothing those countries can do to retaliate effectively. Saudi Arabia, Canada is learning, can retaliate.

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Tom McCuin is a strategic communication consultant and retired Army Reserve Civil Affairs and Public Affairs officer whose career includes serving with the Malaysian Battle Group in Bosnia, two tours in Afghanistan, and three years in the Office of the Chief of Public Affairs in the Pentagon. When he’s not devouring political news, he enjoys sailboat racing and umpiring Little League games (except the ones his son plays in) in Alexandria, Va. Follow him on Twitter at @tommccuin