Congress faces the ultimate trifecta of deadlines this week: The debt limit, highway funding and the likely end of Speaker John Boehner John Andrew BoehnerLongtime House parliamentarian to step down Five things we learned from this year's primaries Bad blood between Pelosi, Meadows complicates coronavirus talks MORE's tenure.

Boehner plans to depart Oct. 30 after 24 years in Congress, one day after the House is scheduled to elect a new Speaker. But in one of his final tasks before heading for the exits, the Ohio Republican is expected to guide the House through the vexing task of raising the debt limit.

Rep. Paul Ryan Paul Davis RyanKenosha will be a good bellwether in 2020 At indoor rally, Pence says election runs through Wisconsin Juan Williams: Breaking down the debates MORE (R-Wis.), the House Ways and Means Committee chairman and 2012 vice presidential nominee, is expected to emerge as the winner during a closed-door GOP conference election on Wednesday. He'll then have to secure 218 votes on the House floor Thursday.

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At this point, Ryan appears to have support across the divided House GOP conference to win the Speaker election. Ryan last week secured endorsements from the conservative Republican Study Committee and centrist Tuesday Group, along with support from a supermajority of the hard-line Freedom Caucus.

About 70 percent of the Freedom Caucus is said to be behind Ryan, which fell short of the 80 percent necessary for an official endorsement that Ryan originally demanded as one of his conditions to run for Speaker. But Ryan ultimately concluded 70 percent support showed enough GOP unity for him to move ahead with a job he has said he never wanted.

Still, there will be a handful of holdouts in the conference election and on the floor. Some conservatives still plan to support long-shot Rep. Daniel Webster (R-Fla.) for Speaker, who remains in the race. And some Tea Party groups have been trying to gin up opposition against Ryan in recent days.

Assuming Ryan clinches the House GOP's nomination, this week will be just the fifth time in the last century the House has voted to elect a new Speaker midway through a term.

Debt limit

Overseeing the House GOP's strategy on the debt limit may be a fitting bookend for Boehner's tumultuous tenure as Speaker since 2011.

It's unclear what Republicans will do ahead of the looming Nov. 3 deadline. House GOP leaders last week had to scrap a Republican Study Committee plan that would raise the debt limit into 2017 but came attached to a slew of conservative reforms.

Many rank-and-file GOP lawmakers are increasingly resigned to an endgame of voting on a clean debt limit bill without preconditions, but it's unclear if such a measure could actually pass the House. Most Republicans are loath to hike the debt limit without including any spending reforms.

Senate Republicans are signaling that they could be forced to move first if their counterparts in the House can't reach an agreement on legislation.

"At some point we probably can't afford to wait any longer," Senate Majority Whip John Cornyn (R-Texas) told reporters last week. "I don't know exactly what the drop-dead date is but something needs to start moving here pretty soon."

Senate Minority Leader Harry Reid (D-Nev.) has demanded that lawmakers take up a clean debt-ceiling bill, though Majority Leader Mitch McConnell (R-Ky.) is opposed to the proposal.

Cornyn added that if the Senate introduces its own legislation, it wouldn't start as a clean bill, but that senators would be allowed to offer amendments. McConnell, meanwhile, sidestepped a question last week on whether or not anything besides a clean bill would be able to pass the chamber.

White House spokesman Eric Schultz told reporters on Friday that Obama would veto any bill that included spending cuts, adding that "we believe this should be done without negotiation, without drama, without delay."

Highway funding

Congress is expected to approve yet another short-term patch before the Highway Trust Fund runs out on Thursday.

The Department of Transportation has warned that it will have to stop making payments to states and local governments for infrastructure projects next month if lawmakers miss the deadline.

The House Transportation and Infrastructure Committee approved a bipartisan six-year highway funding bill last week, but lawmakers still have to work out differences with their counterparts in the upper chamber, who authored a six-year measure over the summer that provided only three years' worth of revenue.

Export-Import Bank

The House is expected to vote Monday to reauthorize the Export-Import Bank after its charter lapsed on June 30, following a rare procedural tactic used by centrist GOP lawmakers frustrated by conservatives in their party.

More than 30 Republicans joined with Democrats to secure the 218 supporters necessary to force a vote, a tactic known as a discharge petition.

But it's unclear if the House vote will be anything more than symbolic. Senate Majority Leader Mitch McConnell (R-Ky.) opposes Ex-Im but has said he would be open to a vote. However, he has said he would prefer attaching it to another bill, such as highway funding.

Cybersecurity

The Senate is expected to wrap up its work on a controversial cyber bill known as the Cybersecurity Information Sharing Act (CISA) on Tuesday afternoon.

The legislation — which is aimed at increasing information sharing between the government and businesses on cyber threats — has received pushback from privacy advocates, including Sen. Ron Wyden (D-Ore.).

The proposal still has to overcome procedural hurdles before it can get a final vote. The Republican leader also scheduled a final vote on a managers package that includes a slate of amendments, as well as votes on seven separate amendments.

Lawmakers will also need to agree to end debate on CISA, which will require the support of 60 senators.

The Obama administration officially endorsed the legislation last week, though it's been unofficially on board with the proposal for months.

“An important building block for improving the nation’s cybersecurity is ensuring that private entities can collaborate to share timely cyber threat information with each other and the federal government,” said a White House memo.

But, it noted that it will "strongly oppose" any push to authorize more exceptions to the Department of Homeland Security “portal,” which could occur under an amendment from Sen. Tom Cotton (R-Ark.).