The Organization for the Prohibition of Chemical Weapons (OPCW) has set an ambitious Dec. 31deadline for Syria to hand over the deadliest of its chemical armaments, which are supposed to be packed into roughly 150 shipping containers, driven to the Syrian port city of Latakia, loaded onto Norwegian and Danish cargo ships and then transported to a location outside of Syria. Once there, they will be transferred to an American vessel called the Cape Ray for destruction. Senior American defense officials stressed Thursday that the Cape Ray itself won’t dock at Latakia and that no U.S. personnel would set foot in Syria.

That, at least, is how the plan is supposed to work in theory. In practice, the effort faces an array of technical, diplomatic, security, and financial challenges. The disposal equipment being installed onto the Cape Ray has never been tested at sea, and it’s not clear that it will be capable of operating continuously for months without breaking down. The U.S. and its allies will also need to find a way of ensuring that none of the weapons are stolen or damaged on their way to the Cape Ray or during the actual destruction work. To say it will be a challenge is the grossest of understatements.

“I know we have a deadline in three weeks but the operations have not yet started,” said one diplomat familiar with the U.N.’s internal discussions. “It’s never going to happen.”

The Obama administration’s more immediate task is to find an allied government willing to allow the ship from Latakia to land at one its ports and unload the weapons before they’re transferred to the Cape Ray. It would take roughly two days to load the weapons onto the American vessel, which means they’d need to be stored at the port temporarily, posing a potential security risk to the host country. Not surprisingly, it’s been hard to convince a government to let a weapons-laden cargo ship unload at one of its ports. That makes it highly unlikely that the U.S. and its allies will be able to meet the Dec. 31 deadline, set by the OPCW, to remove Syria’s chemical arsenal.

Washington recently informed one ally that it was considering using a port servicing a U.S. naval base in Naples, Italy. Talks are also underway with Morocco and Spain to see whether the materials could be unloaded there. Sigrid Kaag, the Dutch head of a joint mission of experts from the United Nations and the OPCW overseeing the elimination of Syria’s chemical weapons, said she wouldn’t speculate about whether the armaments would be transferred to American custody in a Mediterranean port. Pentagon officials said negotiations with foreign governments were ongoing but declined to comment on which countries could ultimately take the weapons before they were transferred to the Cape Ray.

There’s also considerable uncertainty about how the materials will get to Latakia in the first place. The U.S. and other Western powers responded coolly to a Syrian request for armored vehicles and other protective equipment Damascus claimed it needed to carry out a successful operation. In a November 15 letter to the Security Council, Kaag said that Syria would have to reach out to friendly countries for assistance in securing the route. Russia, one of Syria’s closest diplomatic allies, is looking into the possibility of supplying up to 200 trucks to transport the materials. A spokesman for the OPCW, Christian Chartier, said Kaag was trying to act as a “go between” to encourage other states to help Syria with its security needs.

Renewed combat along the route to the port city poses another challenge. During a recent visit to Syria, Kaag told the U.N. Security Council in a closed-door briefing, she was not able to reach Latakia by the main road from Homs — a key hub on the chemical weapons route — because of fighting, forcing her to travel by helicopter from Beirut.

“It’s a main artery, as you know. If we cannot travel there, it’s a real issue,” said Kaag, who is required to travel in the region with a Romanian close protection detail. Kaag insisted that the mission was “all very manageable,” but conceded she could not certain it would go smoothly.

“I’m not aware that this operation has ever been carried out in this way,” she said.

Sending the chemical weapons out of Syria marks the most dangerous, and the most expensive phase of a landmark Sept. 14 pact between U.S. Secretary of State John F. Kerry and Russian Foreign Minister Sergei Lavrov calling for the destruction of Syria’s chemical weapons program by the middle of 2014. (Merely destroying the waste products could cost an estimated 35 to 40 million Euros; the full cost of transporting the armaments out of Syria and destroying them is likely to be exponentially higher).

The accord — which averted a U.S. strike against Syria in retaliation for using sarin to kill hundreds of its own civilians in late August — has proceeded smoothly. On October, 31, Syria effectively destroyed its declared chemical weapons production facilities and mixing and filling plants, the OPCW confirmed.

The U.N. has said the chemical weapons should be packed for transport by Dec. 13 and then moved out of Syria altogether by Dec. 31. A senior U.S. defense official called that timeline “ambitious,” but expressed confidence that it could be met. The destruction efforts would begin aboard the Cape Ray in early January.

Senior defense officials said it would take 45-90 days to turn the weapons into non-harmful waste using two of the so-called “Field Deployable Hydrolysis Systems” that are being installed in the Cape Ray’s cargo holds. The equipment will operate inside of a sealed tent to prevent any of the chemical agents from being accidentally dispersed while they’re being turned into waste. The resulting sludge, in turn, will be brought to a commercial destruction facility elsewhere in the world and then incinerated.

Beyond the difficulty in finding a port where the weapons can be unloaded, U.N.-based diplomats say the United States has also been unable to help secure sufficient funding to hire companies to dispose of the toxic waste products.

“The U.S. or Paris can say that we need to make the deadline but will they ensure they can make it possible?” another official asked, adding that governments “have to be realistic and feasible about the deadlines they impose.”

As of Nov. 30, 35 companies had submitted expressions of interest in securing a contract to collect the waste product from the United States and transfer it to a facility for incineration. But OPCW officials noted that there isn’t enough money in a trust fund established for the destruction of Syria’s chemical weapons to put out formal requests for bids from the firms.

“What I know is that what we have by now is just not enough; it’s far away from being enough,” said Chartier, the organization’s spokesman. “We need to be certain of our financial commitments in order to start the tender process.”

 This post first appeared at Foreign Policy