The Supreme Court deadlock that led to the defeat of President Barack Obama’s plan to shield millions of people from deportation was just the latest judicial check on the ambitions of his administration.

Earlier this week, a federal judge in Wyoming blocked an Interior Department rulesetting stricter standards for hydraulic fracturing on public lands. That decision followed another Supreme Court ruling in February suspending a major regulation limiting carbon emissions from power plants.

In October, a federal appeals court halted an Environmental Protection Agency regulation that would bring more waterways and wetlands under federal protection.

Critics of Mr. Obama have characterized his efforts on immigration and the environment as excessive and illegal. Administration officials have described his agenda as entirely necessary to solving the nation’s problems in the face of congressional inaction.

All presidents push on the boundaries of presidential power, in part because it is a fluid thing, as Justice Robert H. Jackson wrote in his 1952 concurring opinion in Youngstown Sheet & Tube Co. v. Sawyer, which still stands as the most authoritative statement about the scope of executive authority.

When a president acts with express or implied authorization of Congress, his authority is at its zenith, but when he acts against the will of the legislative branch, his power is at its “lowest ebb,” Justice Jackson wrote.

He added that there is a middle area—“the zone of twilight”—where presidents act without congressional approval or disapproval. Presidents can issue executive directives, which are legally binding orders, and rules and regulations. Courts analyze executive orders on a case-by-case basis, using Justice Jackson’s framework.

“Many of these questions about whether the president violated the law are technical. They turn on the meaning of statutes and constitutional provisions that are not widely litigated or discussed,” said Nicholas Bagley, a law professor at the University of Michigan and former Justice Department lawyer. “It can be very difficult to cut through the thicket.”

In the Youngstown case, the Supreme Court held that President Harry Truman exceeded his authority when he seized steel mills to avoid a strike he believed would disrupt weapons production during the Korean War.

Thursday’s 4-4 split on the legality of Mr. Obama’s immigration directive—which would offer temporary protection against deportation and authorize work permits to more than four million immigrants who came to the U.S. illegally, most of them parents of U.S. citizens— preserved the ruling of the Fifth U.S. Circuit Court of Appeals, which blocked the program in November. It ruled the Immigration and Nationality Act, passed by Congress in 1952, “flatly does not permit the reclassification of millions of illegal aliens as lawfully present and thereby make them newly eligible for a host of federal and state benefits, including work authorization.”

While the Obama administration has suffered setbacks in recent days, such rulings aren’t unusual. “These kind of disputes between the president and others are common, and they have been common for decades now,” Mr. Bagley said, though he added that partisan polarization may be stoking more conflicts now than in the past.

Mr. Obama had issued 242 executive orders as of May 20, compared with President George W. Bush’s 291, according to the American Presidency Project, a group that tracks presidential actions.

The Supreme Court tore up Mr. Bush’s plans to try Guantanamo Bay detainees before military commissions, ruling in 2006 that neither federal law nor international law permitted them as conceived. The following year, the high court held that the Bush administration was required to regulate greenhouse gases unless it had a scientific basis for its refusal.

“There is sometimes the view that the president is the CEO of the country,” said Tom C.W. Lin, a law professor at Temple University. But the “way our founders set up the government means that no one individual, no one branch, can dictate the national agenda and can make laws unchecked.”