Canadian Prime Minister Mark Carney is heading to Washington for his second visit this year - this time with the more modest goal of getting trade talks back on track.
Negotiations have dragged on over the summer, blowing past an August deadline set by the two leaders. But few details have been released about the discussions or the issues preventing a deal.
Canada is the only G7 country yet to reach a trade deal with Trump this year - though unlike other allies, Ottawa is not in a rush given carve-outs under the US-Canada-Mexico Free Trade Agreement.
But Tuesday's tête-à-tête comes as Trump has renewed talk of making Canada a US state, while Carney's main opposition figure has said anything short of reaching a trade deal on this trip would be considered a failure.
Canada-US Trade Minister Dominic LeBlanc said last week that progress is being made toward an agreement, and media reports suggest there may be some relief from the punishing US steel tariffs to come.
Insiders have hinted at frustration over a lack of clarity from the White House on what a trade and security deal with Canada could look like.
Face-to-face time with the president, who finds personal relationships important, could help ease the trade stalemate, noted Jamie Tronnes of the Center for North American Prosperity and Security.
At the White House on Monday, Trump said only that I guess he's going to ask about tariffs while highlighting the movement of Canadian companies into the United States.
Carney has faced domestic pressure to secure a deal with the US that would lower tariffs, especially for hard-hit sectors like steel and lumber.
In an open letter to the prime minister ahead of his Washington visit, Conservative opposition leader Pierre Poilievre urged Carney to negotiate a win or risk failing the country's workers and businesses.
Still, Carney has described the relationship with Trump as good and noted the two routinely communicate through text.
As consultations begin ahead of a review of the USMCA free trade agreement, experts predict the US might seek commitments from Canada extending beyond trade into defense cooperation.
Determining what the US wants out of these talks has been complex, with potential industrial and defense agreements on the table.
With 75% of Canada's goods exported to the US and thousands of jobs in vulnerable sectors at stake, Carney's efforts in Washington will be pivotal for economic stability and diplomatic relations going forward.