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REUTERS/Kevin Lamarque
President Obama boards Air Force One after his Martha's Vineyard, Massachusetts, vacation on Aug. 17.
The Obama administration has given the green light for surveillance flights over eastern Syria to prepare for possible military strikes on the extremist militant group ISIS. 
Any increased U.S. involvement in “somebody else’s civil war” at this point brings risks, especially when airstrikes alone would not be enough to beat ISIS and no real policy has emerged to deal with the militants in Syria.
"Senior officials have talked of efforts to 'stall,' 'contain,' 'degrade,' 'defeat,' and 'destroy' the Islamic State. These words actually mean very different things, indicating either a major internal administration debate or utter confusion," Michael Gerson, a senior White House policy adviser from 2000 through June 2006, wrote recently.
Assad, on the other hand, clearly has a plan. The Iranian-backed ruler has offered to work with the West against ISIS — after facilitating the group's rise — while also attempting to destroy what remains of the mainstream Free Syrian Army (FSA).
"[Assad] would prefer to confront the West with what it would present as a fait accompli: the opposition is dead; ISIS is a greater evil than us; you in the West have no choice but to work with us against this greater evil," Fred Hof, a former special adviser for transition in Syria under then-Secretary of State Hillary Clinton, wrote over the weekend. 
And the relatively moderate opposition forces are currently being squeezed by both Assad's troops and ISIS fighters in Syria's largest city of Aleppo, and a new ISIS offensive threatens to cut off FSA rebel supply lines to Turkey. Hussam Marie, the Free Syrian Army spokesman for northern Syria, told The New York Times that the loss of FSA positions in and around Aleppo would be “unrecoverable” and “a blow to our shared goals of a moderate Syria.”
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Wikipedia
Red = Syrian Arab Army; Green = Free Syrian Army and others; Black = ISIS; Yellow = Kurdish forces.
The White House hopes to bolster the FSA with an undefined training mission and strikes on ISIS, but the long-neglected "farmers and dentists" are running out of time.
“We’re going to find ourselves maneuvered into a very uncomfortable position,” Hof told NYT. “We’re unconsciously walking into an ambush."
The situation would look like an intensified version of the State Department's worst-case scenario: "rebel gains evaporating, the moderate opposition ... imploding, large ungoverned spaces [ruled by ISIS], Assad holding on indefinitely, neighbors endangered, and Iran, Hizbollah, and Iraqi militias taking root."
And now that all of that has happened, the administration of President Barack Obama could find itself on the same side of a regime that has tortured and killed people on an industrial scale with no allies on the ground who can beat ISIS.
Consequently, Hof concludes that "if President Obama wishes to avoid the impression that the United States is collaborating with the crime family that has enabled both ISIS and the destruction of Syria, he will direct an immediate and significant resupply of nationalist forces and give the assurances required to encourage the full relocation of Syria's external opposition to Syria itself."
In any case, it is becoming clear that after years of disengaging from the Middle East, Obama is going to need some help. 
"To counter ISIS, the United States must relearn the lessons of the surge [during the Iraq war]," Mike Doran, senior fellow in the Center for Middle East Policy, told Business Insider in an email. "The key is to detach moderate Sunnis, the vast majority of Sunnis, from ISIS, by providing them with security and with a political alternative to rule by Iran and its proxies.
"The first step is to commit the United States, to crushing ISIS unambiguously," Doran continued. "The second step is to create a coalition to achieve that goal by creating a new order in what is now Jihadistan, the region that ISIS controls from Baghdad to Aleppo. That coalition should include, among others, Saudi Arabia, Turkey, Jordan, France, Britain, and, of course, the Free Syrian Army."