President Donald Trump faces multiple deadlines that could immensely complicate his attempt to renegotiate a much-improved trade deal with Canada and Mexico.

The North American Free Trade Agreement (NAFTA) among the three countries was approved in 1994. Trump has been highly critical of it, arguing that it has hurt domestic workers by encouraging firms to ship jobs and manufacturing facilities out of the U.S.

Trump has threatened to withdraw the U.S. from the deal numerous times as he has worked to create a new version.

But getting the three nations to agree on what a new deal should look like is anything but easy, and, as the talks stretch out, legislative deadlines and upcoming elections make the prospect of a successful negotiation appear remote.

“The U.S. and our counterparts are having a hard time coming to an agreement,” Jacqueline Varas, the director of immigration and trade policy at the center-Right American Action Forum, told LifeZette. “And that what’s been reported recently, too, a failure to meet in the middle. But I think that NAFTA is so important to this continent that I don’t see them not getting a deal done. Now, will it be this year, I really don’t think so.”

The Trade Promotion Authority (TPA) imposes some of the more significant time constraints. It gives the president room to negotiate a deal that will be fast-tracked through the Senate for a simple up or down vote without amendments.

“Just based on the economic impact alone, it doesn’t make sense that we have to deal with a deadline,” Varas said. “That’s not in the interest of the United States, Mexico, or Canada. So based on that, I’m pretty confident, at least in my opinion, that something will happen.”

The TPA has a hard deadline that is set to expire July 1, though it can be extended. House Speaker Paul Ryan also imposed a May 17 deadline, which the president has already missed. Trump faces another deadline in that he must report to lawmakers at least 180 days in advance, which means he must submit something by June 15 since the legislative session ends December 13.

“They have about one month,” Dr. Tony Payan, director of the Mexico Center at the Rice University’s Baker Institute, told LifeZette. “On July 1st, President Trump runs out of the TPA. So his ability to renegotiate NAFTA runs out unless Congress approves an extension of the TPA.”

Vanderbilt University Law School professor Tim Meyer said much of the process will depend on the midterm election and how much hardball the administration is willing to play. Trump has shown little interest in providing concessions and has used the pullout threat to push his objectives.

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“There are a couple of deadlines related to TPA,” Meyer told LifeZette. “Part of the reason it’s a moving target is because Congress has a maximum number of days it can spend considering the agreement, but they can shorten the time they take, so there is a question about how much they can shorten it. I think that is a real concern. I think that if the House of Representatives were to change hands and the Democrats were to come in, it would be a much more difficult vote.”

Canadian Foreign Minister Chrystia Freeland visited Washington, D.C., to meet with lawmakers and administration officials amid these multiple deadlines. But the visit appeared to hit a rough patch Thursday with Freeland’s responding to tariff actions by Secretary of Commerce Wilbur Ross by promising proportional countertariffs, reported CNBC.

Payan said Canadian officials are likely bracing for NAFTA’s end and may be considering backup plans to ensure the two countries can still reach a trade agreement. Freeland was likely trying to gauge how U.S. lawmakers were leaning by meeting with them this week.

“I think that it is almost too late, it’s June 1st,” Payan said. “The election in the United States is upon us. We don’t know what is going to happen in Congress. We don’t know whether Republicans are going to maintain control of Congress.”

Democrats could also gain a congressional majority with the midterm voting, which would make it even more difficult to get a trade deal approved or TPA extended. The Mexican presidential election, on July 1, adds yet another complicating deadline for the talks.

Mexican presidential candidate Andrés Manuel López Obrador has been highly critical of NAFTA as he has worked to unseat President Enrique Peña Nieto. Obrador is a bit like Trump in that he is an economic nationalist who promises to put his country first on trade deals.

“On July 1st, in about a month if Mr. Obrador wins the election, there are a couple [of] scenarios that could happen,” Payan said. “I think rightly, Mr. Obrador has said that it should be his team negotiating NAFTA because he’s very confident he’s going to win the election in Mexico and he thinks it is, to a large extent, unfair to have a lame duck administration, the Peña administration, negotiate an agreement, pass it quickly and then saddle him with an agreement he didn’t have any say on.”

Connor D. Wolf covers Congress and national politics and can be reached at [email protected]. Follow him on Twitter