Before President Obama left for his 17-day vacation in Hawaii, White House officials made it clear that his holiday reading would consist of a lot more than beach novels to escape the stresses of Washington. He’d also be studying a 300-page report on how to rein in the government’s controversial surveillance programs that had just been delivered to him by a high-level panel of experts.

Sure, Obama has gotten in plenty of rounds of golf with his presidential posse, as well as impromptu trips to shave ice joints and leisurely strolls along the islands’ stunning beaches with his family. But weighing on him throughout the winter getaway has been one of the most consequential national security decisions of his presidency: whether to adopt a set of recommendations that would represent the most dramatic curbing of the intelligence community’s eavesdropping powers since the Vietnam War.

This has been an especially rough year for Obama, with the government shutdown, brinksmanship over the debt ceiling, a domestic agenda that largely ground to a halt, and the famously troubled health-care rollout. But no issue has created more sustained pain for the administration than the torrent of leaks about the government’s electronic spying programs by former National Security Agency contractor Edward Snowden.

And none cuts more to the core of Obama’s identity as a leader. How will he reconcile the tensions between protecting the American people from terrorism and preserving their fundamental rights to privacy and personal liberty? Will he be remembered as the liberal constitutionalist who restored American values to the war on terror or as a warrior-president who presided over and enhanced the surveillance state?

Obama, of course, has been here before. Throughout his presidency he has struggled, even agonized, over how to balance security and liberty in an age of terror.

No set of policies has bedeviled him more than counterterrorism. He raised the hopes of liberals and civil libertarians during the 2008 campaign, promising to shutter Guantanamo, use civilian courts to try terrorists, and enhance transparency in the use of national security powers. But those constituencies were disappointed after he took office when, in the face of stiff congressional opposition, he continued many of the same policies he had criticized when George W. Bush was president.

Still, behind the scenes, Obama's counterterrorism polices have continued to tug at his conscience. He has prodded his aides to re-address unfulfilled promises and occasionally chastised himself for not acting more in accordance with his personal convictions. His recent vow to “go back at” closing Guantanamo has led to the most sustained progress toward closing the detention facility since the first year of his presidency.

Obama’s willingness to go back and reform his own counterterrorism policies sometimes has led him to give up power or place it under tighter constraints, an unusual characteristic, given that most presidents try to enhance executive authority, especially in the national security arena. Obama, on the contrary, ordered a policy review toward the end of his first term that eventually placed greater restraints on his targeted killing program, resulting in fewer strikes.

His trajectory on surveillance fits the pattern. As a senator and as a presidential candidate during the 2008 campaign, Obama harshly criticized the Bush administration’s warrantless wiretapping program. But shortly after taking office, he was persuaded by officials that the programs had been placed on a firmer legal foundation and were necessary. He had been briefed on occasional compliance lapses so serious that the secret court overseeing the surveillance programs had threatened to shut them down. But each time he was reassured that no harm was done.

There is no evidence to suggest that Obama expressed much skepticism about the surveillance program during his first term. He was assured on several occasions that the NSA’s bulk metadata program, which tapped the phone records—though not the content—of virtually all Americans, was a vital tool for foiling terrorist attacks in the United States.

It was only after Snowden’s revelations and the uproar over the disclosures that Obama began seriously to probe his own administration’s policies. Even then, he publicly backed the programs and said they were essential tools in the fight against terrorism.

But behind the scenes, Obama was showing some irritation with the intelligence leadership that had pressed for these capabilities and repeatedly vouched for their value. One story that rocketed around the intelligence community involved a meeting between the president and NSA Director Keith Alexander. Alexander, who holds advanced degrees in physics and electronic warfare, was trying to explain certain aspects of one of the surveillance programs to Obama. As his highly technical and jargon-laden presentation rambled on, Obama was beginning to lose patience. When Alexander finished, the president thanked him and then icily asked if he could do it over again, “but this time in English.”

While it went unstated at the time, Obama may have felt frustrated that the complexity of the technology was overwhelming policymakers. Even Alexander had publicly conceded that no single person at the NSA had the wherewithal to understand the metadata program in all its dimensions.

By last August, Obama decided he wanted an independent review of the programs and a roadmap for reform. His worry was not that the government had abused the privacy rights and civil liberties of Americans. Rather, according to a top administration official who has spoken to the president about that issue, Obama was concerned that the flood of leaks had badly eroded trust in the intelligence community. He came to believe that restoring that trust was in the vital national security interests of the country.

Some accused Obama of engaging in a public relations exercise by appointing a panel filled with people he knew personally and had worked with. But administration officials and panel members say he in no way sought to tilt the outcome in one direction or the other. In the end, he got 46 recommendations that, all told, would fundamentally, if not radically, restructure and rein in the government’s most intrusive surveillance polices. The question now is, will he adopt them?

As Obama was preparing to leave for his Hawaiian holiday, he gave the public a small glimpse into his thinking about that question. At his final press conference of the year, he was asked about his review panel’s recommendations. He seemed to hint that he might be ready to make changes to the metadata program and that he was open to the panel’s recommendation that the data be maintained by the telephone companies or a private third-party entity rather than the government. “There may be another way of skinning the cat,” Obama said.

Meeting with the review group a few days before, Obama had shown a little more leg. As he walked briskly into the Situation Room last Wednesday, he characteristically wasted little time on small talk. He said he had five points he wanted to make and, without notes, began ticking them off, according to two people who were in the room. Much of what he had to say involved process—now that the recommendations were on the table, he would have to lead an interagency debate to develop a new set of policies. According to one panel member, Obama said he needed to hear whatever objections there were and “probe them.” And he wanted to make sure that those who objected to the recommendations fully understood them.

But he also talked about the substance of the proposals and assessed their viability within the administration. He said he believed the bulk of the 46 recommendations would be acceptable to the intelligence community. He also said many of the recommendations toward the back end of the panel’s report could be adopted easily, including new procedures for establishing secure networks without infringing on Internet freedom and improving vetting and security clearances in hiring. He even mentioned a specific number, amounting to roughly 75 percent of the 46 recommendations, that he thought could be adopted without any problem.

A number of panel members, speaking anonymously, said they had the clear impression that Obama was personally inclined to back their proposals on ending the metadata program, as well as many of the other recommendations that would rein in the NSA’s surveillance capabilities. “The question is whether he will be able to resist whatever pushback comes from the intelligence community,” said one panel member.

Some of that resistance is already coming at a furious pace. One recommendation that has provoked considerable alarm within the FBI would require that National Security Letters be approved by a federal judge before they could be issued. NSLs are similar to grand jury subpoenas in criminal cases, though the FBI can issue them now unilaterally without any judicial approval. They have existed for decades but were dramatically expanded when Congress passed the Patriot Act after 9/11. The letters, which are issued secretly, compel companies to turn over vast amounts of data, such as subscriber information, financial data, and Internet habits. They are deeply unpopular among civil libertarians but are considered a vital terrorism tool by the FBI.

The bureau has argued that requiring NSLs to be approved judicially will make the process of getting critical information slow and cumbersome. But that, in a way, is exactly the idea, some in the review group say. “Part of the point of requiring law enforcement officials to go to a judge for approval is not only to have the neutral, detached determination of a judicial officer but to be inefficient,” says Geoffrey Stone, a panel member and law professor at the University of Chicago. “That slows down the process to provide an opportunity for careful deliberation rather than rushing to do something without giving sufficient thought to whether it’s lawful.” Adds Stone: “Inefficiency is a way of achieving freedom.”

Still, a senior Justice Department official says the FBI is mounting a major effort to preserve its ability to issue the letters free of judicial interference. “The bureau is going to dig in on this one,” says the source.

It is unclear how aggressively the NSA will fight the proposal to end the metadata program. When Alexander met with the review panel, he left its members with the clear impression that he would be fine with relinquishing the program with all its burdensome requirements and endless bad PR. Moreover, Alexander and his deputy, John Inglis, have let it be known that they are planning to resign from the government in the next few months, so they may have less incentive to push back on the issue.

But Obama will likely face strenuous opposition on the metadata program from other quarters, notably from the telephone companies and some privacy groups. Private carriers such as AT&T and Verizon are vehemently opposed to the proposal that they hold onto the telephone data, saying that doing so will impose intolerable financial burdens and litigation risks on them. Without congressional legislation that limits the uses of the database to terrorism cases, they argue, they would be inundated with search requests from local law prosecutors, police, and even divorce lawyers.

Members of Obama’s review group, who are scheduled to testify on Capitol Hill in the second week of January, are gearing up for a fight. “The problems cited by the carriers are such red herrings that it is laughable that they would trot them out,” says Richard Clarke, a member of the panel who has advised three presidents on counterterrorism policies. Clarke contends that Congress would pass legislation defraying the costs of maintaining the database and proscribing the uses of the metadata “in a nanosecond.”

In the end, members of the review group believe that their fight to reform the government’s surveillance policies will be won or lost not so much on the merits of the individual policies but on the larger principle that Americans need to have confidence in their intelligence agencies. “We made the point to him at our meeting that facts alone are not the only thing to take into account,” recalled one member of the panel. “Perceptions matter, too, and they have been changed by these revelations. We have to change the perception among our citizens that the intelligence agencies can’t be trusted.”

Obama was “poker faced” during this part of the discussion. But it seemed clear from the comments he made at his press conference two days later that he agreed with the message. Without conceding that the NSA had ever abused its power, Obama identified his main task as trying to find out how the government can achieve its goal of safeguarding the American people “in ways that give the public more confidence that in fact the NSA is doing what it’s supposed to be doing.”

Sometime in January, Obama plans to deliver a major speech laying out his own blueprint for surveillance reform. By then, the gently swaying palm trees and soft sand of his Hawaiian vacation will be a fading memory.