Few in Biden’s orbit have ever met Johnson, a religious conservative who was largely unknown until his stunning ascent to the speakership. And while the West Wing didn’t appreciate former Speaker Kevin McCarthy’s grandstanding, they did feel like he eventually wanted to deal — and they are less sure about Johnson, according to the officials. Moreover, the same fringe group of Republicans who ousted McCarthy wield that same power over Johnson — and they are largely opposed to helping Ukraine, making a path to deal that much more difficult.

“People are well aware that if a vote were put up in the House of Representatives today, it would pass with an overwhelming majority of members — that the issue is not the level of support as it is getting to that vote,” said Rep. Jason Crow (D-Colo.). “Because of the political conditions and the change in leadership, getting the vote has been the hard part.”

On two occasions already, Democrats tried but failed to get aid to Ukraine in a must-pass funding bill. With another deadline to spark action not coming until the latest stopgap funding bills expire in late January and early February, many of Congress’ strongest Ukraine backers fear the country can’t wait that long.

“I don’t know that Ukraine can survive until February of 2024,” Sen. Chris Murphy (D-Conn.) said. “My sense is they start to run short on ammunition in the next several weeks.”

Believing there is an immediate need, Ukraine advocates are gearing up for a standalone Senate vote on funding when they return from break. Should that vote happen, it would provide a massive test both for the administration’s ability to work Capitol Hill and one of the bedrock elements of the president’s foreign policy agenda.

But the main obstacle still remains: what to do about Republican opposition.

Since passage of the last Ukraine supplemental, Kyiv’s counteroffensive has stalled and conservative support in Washington has crumbled with the GOP’s leader, Donald Trump, opposing it. The outbreak of war in the Middle East has led to the addition of aid to Israel — and growing demands by progressive Democrats for a cease-fire and conditions on aid to Israel.

While support for Israel has strong support in both chambers, senators and administration officials insist that Israel and Ukraine funding remain together.

The thornier challenge is meeting the Republican demand that the package address border policy. The administration’s request includes funding for border security, but the GOP insists it include policy changes to stem the number of people crossing the border, too.

“If Republicans want to have a serious conversation about reforms that will improve our immigration system, we are open to a discussion,” a White House spokesperson said. “We disagree with many of the policies contained in the Senate Republican border proposal. Further, we do not see anything in their proposal about creating an earned path to citizenship for Dreamers and others.”

The bipartisan group of lawmakers who are trying to negotiate a border compromise have continued to talk over the Thanksgiving break, according to a Senate aide. But for many lawmakers, the initial meetings before the holiday only brought the challenge into clearer view.

“They’ve been frustrating,” Sen. Lindsey Graham of South Carolina, one of the lead Republicans in the group, said of the discussions. “We’ll see what happens. I’m not going to support an appropriation supplemental that doesn’t have real border security.”

Democratic Ukraine supporters have embraced the idea that they must include border policy reforms. And while they don’t like marrying the two unrelated issues, they do see an upside if they’re able to address the political thorny issue of the border.

“This is really important funding. I think it’s important for the civilized world to take a stand against dictators like Vladimir Putin and terrorist groups like Hamas,” Sen. Jeanne Shaheen (D-N.H.) said. “And I also think we have a failed policy at the southern border, and we need to look at ways to fix it.”

The White House is not directly involved in the border conversations, but officials have expressed support for them publicly and privately, according to several people involved in the discussions.

“President Biden and the leaders in the Senate, both Republican and Democrat, are rock solid in their support of Ukraine,” Sen. Chris Coons (D-Del.), who is close with Biden, said Tuesday on MSNBC’s “Morning Joe.”

“We have to bear down, get this done and get this supplemental passed soon because the brave Ukrainians who are fighting as winter is coming are looking at losing the supplies they’ve needed for ammunition, for missiles, for drones, for defense, for armor, and we cannot possibly afford to abandon Ukraine,” he added. “If our Republican colleagues demand too much in this negotiation, we won’t be able to get it passed in the Senate and then in the House.”

Senate Minority Leader Mitch McConnell has said border policy must be included in the deal in order to get Ukraine funding through Congress. Inside the White House, McConnell has emerged as an unlikely hero for his steadfast support of Ukraine, which has helped, to a large degree, keep his party in line. But the West Wing has growing fears that the Kentucky senator’s grip on his party has slipped, according to the two senior aides granted anonymity to speak about private discussions.

And a border deal carries risk for Democrats. A chief Republican policy proposal would increase the standard migrants must clear to gain asylum into the United States, an idea strongly opposed by progressives.

“We’ve been the beacon of light around this world for many, many generations, when it comes to people who are fleeing violence and fleeing for the sake of their life,” said Rep. Tony Cárdenas (D-Calif.). “For us to actually weaken that process would be shameful on America. It would be a shame to any member of the House or the Senate that would ever put that on this president’s desk, and I don’t see this president signing a bill with that in it.”

Members of several House caucuses — the Congressional Asian Pacific American, Congressional Black, Congressional Hispanic and Congressional Progressive caucuses — said in a statement earlier this month that they deeply oppose attaching new policy to a funding bill.