The result has often gone far beyond bureaucratic confusion, and has, at times, inflicted painful and unexpected consequences on people's lives.
"It's not something that appreciates these young children and was certainly done in a 'ready, fire, aim' way, obviously," said Republican Senator Bob Corker of Tennessee, describing the Administration's immigration policy. "There was no preparation for it."
Trump implemented a major new policy with no apparent plan or new resources to handle the influx of people who would be detained and prosecuted as a result.
When a public outcry ensued, the Administration could not answer basic questions about it. Trump then changed the way the policy worked — leaving officials within the Administration and at the border confused on how to enact the changes. Plus, it took several days for the Government to say how it planned to reunite families and where the separated children were located.
Trump's struggles on immigration follow his failure last year to repeal the so-called Obamacare law, a central tenet of GOP orthodoxy since President Barack Obama signed it into law in 2010, and the President's uneven implementation of his travel ban, which will be the subject of a Supreme Court ruling this week.
New tariffs have strained relationships with European and North American allies and his Middle East peace plan is still under development amid a standoff with the Palestinians after he said the decades-old problem wouldn't be hard to solve.
Trump has often mused since the 2016 presidential campaign that it would be "so easy" to pass a sweeping immigration law and construct a "big, beautiful" border wall, paid for by Mexico.
Last week, he tweeted that his Democratic leadership adversaries in Congress, Senator Chuck Schumer and Congresswoman Nancy Pelosi, would be "forced to do a real deal, so easy, that solves this long time problem."
But the upcoming week could offer fresh evidence that the reality of governing is much more challenging.
Republicans are seeking to steer an immigration bill through the House despite scepticism among conservatives and uncertainty about Trump's commitment to the plan. The President told House Republicans he was "1000 per cent" behind their effort last week but then suggested just three days later on Twitter that Republicans wait until after the Midterm elections.
Congressman Michael McCaul, (R), the chairman of the House Homeland Security Committee, said he received assurances from the White House during the weekend that Trump was "still 100 per cent behind us." But the fate of the bill remains in doubt and it remains unclear if House Republicans could pass a narrower version that would only address the separation of children and their families.
Confusion has lingered over Trump's border policy.
After a public uproar over the "zero tolerance" policy that led to more than 2300 immigrant children being separated from their families near the Mexican border, the President signed an Executive Order last week for the children to be brought back together with their families. The order seeks to keep families together in detention instead of separating them while their legal cases are heard by the courts.
A 1997 landmark case known as the Flores settlement governs how children are handled in immigration custody and generally prevents the government from keeping them in detention, even with their parents, for more than 20 days.
Trump is seeking to amend the agreement to allow for families to be detained indefinitely together. But Justice Department has said the 20-day policy remains in effect until Congress or the courts take action to change that.
That means if Congress fails to pass legislation or the courts decline to change the terms of the settlement, the Administration could be forced to again separate the immigrant children from their parents in three weeks.
Officials have issued conflicting signals over the state of the Administration's policy and some parents have said they don't yet know where there children are.
Trump tweeted that the US "cannot allow all of these people to invade our Country." He said when someone attempts to enter the country illegally, "we must immediately, with no Judges or Court Cases, bring them back from where they came. Our system is a mockery to good immigration policy and Law and Order."
The American Civil Liberties Union said that is both illegal and unconstitutional.
Trump also continued to blame Democrats in the Republican-controlled Congress, urging them to "fix the laws. Don't RESIST."
But Senator Jeff Flake, (R), a frequent Trump critic, said the problem was larger than a partisan fight.
"When the President says that and calls them clowns and losers, how does he expect the Democrats to sit down and work with Republicans on these issues? And so words matter. What the President says matters. And he ought to knock that off," Flake said.
Paul Light, a professor of public service at New York University, said the federal government is not the "agile instrument" for policy that Trump seems to think it is.
"It's very difficult to make a U-turn, then make another U-turn," Light said, adding that's exactly what Trump did last week in signing the Executive Order after he and other Administration had insisted for days that their hands were tied and that only Congress had the power to step in and do something.
"He sees decisions like ordering at McDonald's. You order, it comes, good-bye," Light said. "That's not the way government works."
- AP