A 50 percent US tariff on roughly $20 billion of Canadian goods is due to take effect at midnight unless a trade deal is finalized, and USD/CAD has spent two weeks pricing the outcome ahead of the headlines.

Canada's overall exports to the US fell 5.8 percent. The two disputed categories fell 22 and 81 percent, and that gap is the entire legal case.

Friday's Section 338 deadline runs on entry date, not ship date, and that distinction is the real planning window this week.

Trump paused Section 338 tariffs three hours before the deadline. The market is pricing it as resolved. It isn't.

Trump called off what he described as the biggest strike on Iran since World War Two, then reissued an ultimatum within a day. The chain from that whiplash to Canadian portfolios runs through gasoline prices and the Bank of Canada's September 2 decision as much as through crude oil charts.

Crude has reversed sharply four times in the past month, each time on a headline that got priced as resolution and then was not. The pattern has a name, and it explains why Tuesday's rebound should not be read as an answer either.

Three new Section 338 proclamations put a 50 percent tariff on Canadian dairy, alcohol, and select vehicle categories starting August 19, but the sectors the U.S. chose not to touch say more about where this goes next.

Iran's strikes reached Qatar and Jordan for the first time this week, yet WTI eased for a second straight day. Why the actual tail risk for Canadian energy exposure is not the headline count of countries involved, but a genuine halt in Hormuz shipping.

A sanctions snapback that one specialist says may end the US-Iran agreement has already added more than $5 to WTI, and the Canadian portfolio question is whether this is a contained escalation or the start of the truce's collapse.

WTI has fallen nearly 30% since the Hormuz memorandum was signed. On June 17, Trump warned bombing could resume. The market has not adjusted, and that gap is the tail risk Canadian portfolios are not pricing.

The US-Iran agreement signed June 15 ends the blockade phase and begins a 60-day nuclear negotiation window. For Canadian portfolios, the immediate read-through is lower oil, a recovering loonie, and a BoC that can finally look past its inflation constraint. The tail risk is that the deal does not hold.

The April 8 ceasefire between the US and Iran has effectively collapsed. US strikes on June 9 and 10 resumed the kinetic phase of the conflict. Iran retaliated against US bases in Bahrain, Jordan, and Kuwait. The Strait of Hormuz remains near-closed. For Canadian portfolios, the question is not whether the war premium returns. It is whether the market has correctly priced the duration of the disruption.

Iran struck Kuwait International Airport on June 3, suspended peace talks, and traded strikes with U.S. forces near the Strait of Hormuz. The chain of consequence for Canadian portfolios runs through one variable: whether these escalations threaten the Hormuz supply disruption that has underpinned the energy re-rating since February 28.

WTI at $95 implies the market believes the Iran ceasefire holds and Hormuz reopens. The events of the past 72 hours suggest that confidence is misplaced. The gap between what is priced and what is possible is the risk Canadian energy portfolios are carrying right now.

A 60-day ceasefire extension between the U.S. and Iran is taking shape today, with the Strait of Hormuz set to reopen. Trump has not signed. The deal is not done. But the direction of oil prices is already telling Canadian energy investors what to expect if it is.

The IRGC's Thursday morning strike on a U.S. airbase and a ballistic missile launch toward Kuwait are the most serious ceasefire violations since April. For Canadian energy portfolios that sold off Wednesday on deal optimism, the overnight reversal is not a buying signal -- it is a demonstration of the scenario that has been defining this market since March 4.