Updated

The Obama administration is taking action to reverse U.S. policy toward Syria, a move analysts say is fraught with risks.

Secretary of State Hillary Clinton signaled the change Tuesday when she said the U.S. would send two envoys to the Middle Eastern country to begin "preliminary conversations."

Clinton, calling the overture a "worthwhile effort," said the administration cannot predict what the future holds for U.S.-Syria relations.

But the dispatch of emissaries, including former U.S. ambassador to Lebanon Jeffery Feltman, would mark the highest-level U.S. administration visit in more than four years to Syria, which has been called a state sponsor of terrorism. Syria has been accused of building a secret nuclear reactor that was destroyed by Israeli bombers in 2007 and being behind the assassination of former Lebanese Prime Minister Rafik Hariri in 2005.

"It's a reversal of what we were trying to do," said John Hannah, a senior fellow at The Washington Institute for Near East Policy who, as national security adviser to former Vice President Dick Cheney, worked on Syria policy in the Bush administration.

Hannah said he's skeptical of President Obama's plans, but he added that the gambit could yield a huge payoff if the U.S. is able to extract Syria from the anti-Western coalition in the Middle East, which is led by Iran.

"It's a huge strategic play. It would have dramatic, strategic consequences, I think, if it's in fact viable and doable. And that's the big question."

While bold, the outreach to Syria is not shocking.

Sen. John Kerry, chairman of the Senate Foreign Relations Committee, just returned from a visit to Syria. And Obama has long stated his desire to revive diplomatic talks with nations deemed hostile, stating during his inaugural address that, "we will extend a hand if you are willing to unclench your fist."

Whether Syria will unclench its fist without major, and potentially harmful, U.S. concessions is the big question as Clinton dispatches her envoys.

The U.S.-Syria relationship continued to deteriorate in the Bush administration after years of hostilities.

The United States criticized Syria for supporting groups like Hamas and Hezbollah, and has accused the country of allowing extremists to cross its border to fight U.S.-led forces in Iraq. The Bush administration withdrew the U.S. ambassador to Syria in early 2005 in protest of the Hariri assassination -- Syrian officials have been investigated in the killing, though Damascus denies involvement.

Following international pressure and isolation, Syria recalled its longstanding military forces from Lebanon in mid-2005. But with elections coming up this summer in Lebanon, the country is divided between pro-Western factions once led by Hariri and groups allied with nations like Syria and Iran.

Hannah conceded that the U.S. policy of isolation was faltering toward the end of the Bush administration, but he warned that the U.S. must be careful not to weaken its position in Lebanon during discussions with Syria. He said such an outcome would be disastrous.

Kerry, in a speech to The Brookings Institution on Wednesday, said negotiations with Syria cannot come at the expense of Lebanon. The Massachusetts Democrat added that Syria's long-term interests ultimately lie with the West, not Iran, and he said President Bashar al-Assad told him last month that the country is prepared for peace talks with Israel

Kerry spokesman Frederick Jones told FOXNews.com the U.S. has no illusions about Syria continuing to "have their tentacles" in Lebanon and harbor militants like Hamas' Khaled Mashal.

But he said Syria can play a "constructive role" in the region.

Benjamin Friedman, a fellow in defense and homeland security studies at the Cato Institute, said he doesn't see much of a downside in reaching out to Syria. He said the talks could go nowhere, but they could also lead to Syria cutting back on support for Hezbollah and Hamas.

"It seems unlikely but not impossible," Friedman said.

The most recent high-level U.S. visits to Syria were in January 2005, by Deputy Secretary of State Richard Armitage, and in September 2004, by William Burns, who previously served as an assistant secretary of state and is now under secretary for political affairs at the State Department.

Since then, Syrian ties to the West took a hit when Israeli warplanes destroyed a Syrian site in 2007 that Washington said was a reactor that, once completed, could have produced plutonium.

With the revived outreach, Obama also runs the risk of politicizing the already protracted investigation into the killing of Hariri. The international tribunal to try suspects in the case opened at The Hague on Sunday.

Hannah said the international community holds tremendous leverage over Syria -- and Assad -- with the tribunal, and any trade-offs for cooperation could come at the expense of justice in the Hariri case.

But a potential payoff in wooing Syria would ultimately be to ease the road to peace between Israel and the rest of the region.

In a newly released report for The Brookings Institution, Itamar Rabinovich, former Israeli ambassador to the U.S., wrote that the Bush policy of non-engagement has "failed to work."

Rabinovich wrote that Syria is a small but significant piece of the larger national security puzzle, and that engaging Damascus could be critical for both the U.S. and Israel if efforts to engage Iran fail.

Rabinovich noted that Syrian officials have "alluded" to the position that their ties to Iran are not set in stone and are mainly the product of being shunned by Washington. Rabinovich wrote that Washington can test this position, however delicately.

Asked about Clinton's statements on Syria, Israeli embassy spokesman Jonathan Peled said the country was taking a "wait-and-see" approach.

Clinton suggested during her visit to Israel on Tuesday that she foresees such regional benefits to the talks.

"There are a number of issues that we have between Syria and the United States, as well as the larger regional concerns that Syria obviously poses," Clinton said.

"Again, we don't engage in discussions for the sake of having a conversation. There has to be a purpose to them. There has to be some perceived benefit accruing to the United States and our allies and our shared values."

FOXNews.com's Judson Berger contributed to this report.