"There's a danger that the Taliban will smell weakness," one foreign diplomat told NBC News.
Trump's impulsive nature, along with his openly expressed doubts about the U.S. military mission in Afghanistan, has injected a sense of urgency among senior officials and military officers. The last diplomatic attempt to end the war ended in abject failure in 2013, amid acrimony between Afghanistan's then-President Hamid Karzai and U.S. officials.
Although Trump reluctantly approved the deployment of several thousand additional U.S. troops to Afghanistan last year, he remains skeptical about keeping the 15,000-strong force in place. With no clear military victory in sight, U.S. officials are worried the president could abruptly pull the plug on the mission without advance warning.
"Just because he signed on to this policy in August, most of the people who work for him have no trust and confidence that he'll stick to his policies," said a former senior U.S. official familiar with administration discussions, who spoke on condition of anonymity.
As a result, the administration is now focused on a high-risk diplomatic wager to end the conflict. Spearheaded by Alice Wells, the senior State Department official overseeing South Asia, the diplomacy has featured a series of conversations with major powers in the region as well as contacts with Taliban representatives at venues outside of Afghanistan.
Although the U.S. has maintained a channel to the Taliban over the years, the discussions have become more frequent, more high-level and more ambitious, former U.S. officials and foreign diplomats said. However, the talks are still portrayed as preliminary, designed to set the conditions for an eventual negotiation between the Afghan government and the Taliban.
A senior Afghan Taliban official offered a similar description, saying the meetings are not formal negotiations but are meant to find a way to hold "fruitful and results-oriented peace talks in the future."
The most recent meeting took place within the past week in the Qatari capital of Doha, with Wells leading the U.S. delegation, foreign diplomats said. Taliban sources say meetings have also taken place in the United Arab Emirates.
"We have held a number of meetings with U.S. officials in the past, but never found them this serious for peace talks with us," the Taliban source said. "They conveyed to us a 100 percent green light for peace talks and we decided to meet again very soon."
The former number three-ranking official at the State Department, Thomas Shannon, who helped shape U.S. policy for the region in Trump's first year in office, acknowledged the U.S. dialogue with the Taliban and suggested that the insurgents appear more open to peace talks than in the past.
"Our own engagement with the Taliban has indicated an interest and willingness on their part," Shannon said at the Aspen Security Forum on July 21.
Shannon also credited Afghan President Ashraf Ghani with creating the conditions for possible peace talks and for rallying other governments — including Islamic countries — to the cause.
He said he was not ready to say he was optimistic, but cited positive signs, like a three-day cease-fire last month, that could eventually produce momentum toward peace or at least a winding down of the war.
"I think we are in a position in which there are possibilities and potential out there for political resolutions," said Shannon, who retired from the diplomatic service in February.
“One thing was very positive, that we noticed U.S. authorities seemed very eager to meet again and again to bring peace to Afghanistan.”
Describing the most recent round of talks, the senior Taliban official said the meeting "took place in a very friendly environment and the two sides carefully listened to each other's demands and proposals for future negotiations."
"They wanted us to announce a cease-fire soon after the beginning of the peace process, which we refused," he added. "However, we agreed to meet again somewhere in the United Arab Emirates, Qatar or somewhere else."
He said the meeting was at a high level and lower-ranking Taliban representatives in the Qatar-based office were not invited to it.
"Our Qatar office is like a post office and it is not authorized to make important decisions or hold high-level meetings without the approval of the leadership council," he said. The Taliban will now discuss the proposals in its leadership council meeting and will make decisions for future talks with the U.S., he said.
"One thing was very positive, that we noticed U.S. authorities seemed very eager to meet again and again to bring peace to Afghanistan," he added.
The U.S. side queried the Taliban about its interest in having a role in a future Afghan government, and also discussed the possibility of suspending U.S. military operations in a particular province while peace talks took place, the Taliban official said.
NBC News could not confirm details of the Taliban official's account of the discussions.
The Trump administration has neither confirmed nor denied the discussions with the Taliban but has acknowledged Wells led a U.S. delegation to Qatar a week ago. A State Department spokesperson reiterated the U.S. administration's standard public stance, telling NBC News that "any negotiations over the political future of Afghanistan will be between the Taliban and Afghan government."
Administration officials are keenly aware that any direct outreach to the Taliban runs the risk of alienating their partners in the Afghan government. Anxious to avoid a repeat of the distrust that plagued America's relationship with former Afghan President Karzai, U.S. officials and military officers are going out of their way to keep current Afghan President Ashraf Ghani in the loop and fully briefed on their talks with the Taliban.
"President Karzai thought we were hiding things from him, that we never gave him full readouts," the former U.S. official said.
"With Ghani, we have a much different relationship. Everything we've done, we've told the Afghans about it beforehand."
When media coverage of last month's temporary cease-fire portrayed the U.S. commander in Afghanistan, Gen. John Nicholson, as the mastermind behind the deal, his office promptly issued a statement rejecting that account.
Afghan officials — and other foreign governments — had privately protested to the Trump administration that the news reports could damage Ghani's political position, especially as some of his domestic rivals are critical of any U.S. talks with the Taliban and of Ghani's offers to negotiate without preconditions.
To reassure Kabul, U.S. officials have discussed potential arrangements designed to ensure the Afghan government is not shut out of any negotiations and plays the lead role in hammering out a peace deal with its Taliban foes. One scenario would have the U.S. speak to the Taliban as a first step, with the discussions quickly followed up by talks between Afghan government officials and Taliban leaders, former officials said.
It is also possible a third party, perhaps Saudi Arabia or a United Nations envoy, could act as a mediator for the talks, former officials and foreign diplomats said. The Taliban has long refused offers to negotiate with the Afghan government and has instead demanded direct talks with the U.S. to push for the full withdrawal of American forces from the country.
"The Taliban see us as the big prize. They've always been asking for direct talks with the United States," one former U.S. diplomat said.
Apart from Trump's outlook and desire to see U.S. troops depart, several current and former U.S. officials believe other factors are in play that could present a chance at forging genuine peace negotiations. The three-day cease-fire last month exposed weary foot soldiers in the Taliban insurgency who embraced the chance to venture into towns and snap selfies with Afghan police. And unlike under the Obama administration, the U.S. has set no exit date for American troops while continuing to hammer the Taliban from the air, making it difficult for the insurgents to stage major ground offensives or to simply wait out the U.S.
White House officials, who had been initially wary of the diplomatic push, have endorsed the effort while insisting the U.S. not be seen as overly eager in its dealings with the insurgents, former officials said. Senior U.S. military leaders, who were less enthusiastic for diplomacy when President Barack Obama was in office, have also enthusiastically backed the effort. And in contrast to the previous administration that saw bitter internal battles over Afghan policy pitting the American ambassador against top commanders, senior U.S. diplomats, military officers and White House officials are working in a coherent way and are not bogged down in disputes.
One country that could hold the key to any peace process is neighboring Pakistan, which helped create the Taliban and has remained its key patron, much to the frustration of the U.S. and Afghan governments. Wells has held extensive talks with the Pakistan government and military to urge them to play an active role and help persuade the Taliban to enter into formal negotiations with the Afghan government.
So far, Islamabad has yet to play a constructive role in fostering peace talks, despite repeated appeals from Washington. But it has not sought to sabotage the fledgling diplomacy either, current and former officials said.
Dan De Luce and Courtney Kube reported from Washington, Mushtaq Yusufzai from Peshawar, Pakistan, and F. Brinley Bruton from London.