President Obama’s window for issuing major regulations is beginning to close.

While there is disagreement among experts about the drop-dead date, most say the administration has only until the spring or early summer to pursue additional environmental, health and labor protections before Obama leaves office.

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Sam Batkins, the director of regulatory policy at the conservative American Action Forum, estimated the president has until May 17 to issue regulations without fear that the next Congress or administration will reverse them.

“The administration generally knows this date and is aware of the Congressional Review Act, and members of Congress are aware as well,” he said.

Under the Congressional Review Act (CRA), lawmakers have 60 legislative days to overturn a regulation from the administration.

But if lawmakers are not in session for the 60 days before adjourning their final session, the clock resets, and the new Congress is given another 60 days to act.

That’s the very scenario that took place in 2001, the one time Congress succeeded in using the CRA to overturn a rule.

“It’s been used exactly once at the turn of the administration from Clinton to Bush to overturn [Occupational Safety and Health Administration’s] controversial ergonomics regulation,” said Stuart Shapiro, an associate professor and director of the public policy program at Rutgers University.

But the mere threat of a regulation being reversed is something the administration is eager to avoid, with the White House seeking to craft a legacy for the president that will stand the test of time.

The White House office that reviews all federal regulations has already made a preemptive strike, warning agencies not to engage in what is commonly referred to as “midnight regulations” — when outgoing officials engage in a flurry of rulemaking before cleaning out their desks.

In a memo dated Dec. 17, Howard Shelanski, the administrator of the White House Office of Information and Regulatory Affairs (OIRA), asked agencies to keep their regulatory actions in line with the deadlines that were set in 2015.

“To the extent feasible and consistent with your priorities, statutory obligations and judicial deadlines, however, agencies should strive to complete their highest priority rulemakings by summer 2016 to avail an end-of-year scramble that has the potential to lower the quality of regulations that OIRA receives for review and to tax the resources available for interagency review,” Shelanski’s memo said.

Shelanski urged agencies to consider how long it will take their rule to go into effect once finalized. Agencies often set effective dates 60 to 90 days after a rule is published in the Federal Register, which gives industry groups time to comply.

OIRA did not respond to requests from The Hill to speak with Shelanski.

Susan Dudley, who served as OIRA administrator under President George W. Bush, said she believes Shelanski’s memo is the second time the office has warned agencies against midnight regulations. The first, Dudley said, was in the final year of the Bush administration, when she was still leading the office.

“My sense is [Shelanski’s] trying to achieve an orderly final year and an orderly transition,” Dudley said. “It happens in every transition. At the end, people think of things they just have to do, and OIRA doesn’t have the time to review them.”

A burst of midnight regulations, however, is almost inevitable, experts say.

Shapiro said it’s just human nature for officials to procrastinate.

“I tell my students don’t wait until the last minute with your assignment partly because it won’t be as good,” he said. “There is some evidence that the cost-benefit analyses of midnight regulations are not as strong as they are with your typical regulations.”

The rulemaking process can be lengthy. An agency has to propose a rule, give the public at least 30 days to comment, review the comments, draft the final rule and submit that final rule to OIRA, which has 90 days to review it.

But changing administrations, industry outcry and litigation can all delay the process. It’s been nearly 20 years, for example, since the fight began over a new rule that would limit worker’s exposure to harmful silica dust.

In 2011, OSHA proposed to update the limits that were set in the 1970s and now, five years later, the rule has finally made its way to OIRA for final review.

The threat of a CRA review looms over many of the major Obama regulations moving through the pipeline, including OSHA’s silica dust rule, the Department of Transportation’s fuel efficiency standards for heavy-duty trucks, the Food and Drug Administration’s first-ever rules for cigars and electronic cigarettes and the Department of Energy’s efficiency rules.

But even if the administration can wrap up its major regulatory initiatives before a new president takes office, there’s no guarantee that some won’t be cut down in court.

“There is no date for when the Obama administration could make sure rules aren’t attacked by litigation,” said Rena Steinzor, former president of the liberal Center for Progressive Reform.

“We have something called blood-sport rulemaking, and the notion behind that is you attack a rule from every angle and you keep pounding on it until it doesn’t happen because time is money the more you can delay it.”

As for the Congressional Review Act, Steinzor said the same forces that stymied efforts to roll back regulations through the appropriations process will stand in the way of a CRA resolution.

“I don’t know why it’s viewed so optimistically,” she said.