If the effort advances, one of the next steps would be more public, unequivocal U.S. support for establishing a Taliban office outside of Afghanistan.
U.S. officials said they have told the Taliban they must not use that office for fundraising, propaganda or constructing a shadow government, but only to facilitate future negotiations that could eventually set the stage for the Taliban to reenter Afghan governance.
On Sunday, a senior member of Afghanistan's High Peace Council said the Taliban had indicated it was willing to open an office in an Islamic country.
But underscoring the fragile nature of the multi-sided diplomacy, Karzai on Wednesday announced he was recalling Afghanistan's ambassador to Qatar, after reports that nation was readying the opening of the Taliban office. Afghan officials complained they were left out of the loop.
On a possible transfer of Taliban prisoners long held at Guantanamo, U.S. officials stressed the move would be a 'national decision' made in consultation with the U.S. Congress. Obama is expected to soon sign into law the 2011 defense authorization bill that contains new provisions on detainee policy.
There are slightly fewer that 20 Afghan citizens at Guantanamo, according to various accountings. It is not known which ones might be transferred, nor what assurances the White House has that the Karzai government would keep them in its custody.
Guantanamo detainees have been released to foreign governments--and sometimes set free by them--before. But the transfer as part of a diplomatic negotiation appears unprecedented.
Ten years after the repressive Taliban government was toppled by its Afghan opponents and their Western backers, a hoped-for political settlement has become a centerpiece of the U.S. strategy to end a war that has killed nearly 3,000 foreign troops and cost the Pentagon alone $330 billion.
While Obama's decision to deploy an extra 30,000 troops in 2009-10 helped push the Taliban out of much of its southern heartland, the war is far from over. Militants remain able to slip in and out of lawless areas of Pakistan, where the Taliban's senior leadership is located.
Bold attacks from the Taliban-affiliated Haqqani network have undermined the narrative of improving security and raised questions about how well an inexperienced Afghan military will be able to cope when foreign troops go home.
In that uncertain context, officials say that initial contacts with insurgent representatives since U.S. Secretary of State Hillary Clinton publicly embraced a diplomatic strategy in a February 18, 2011 speech have centered on establishing whether the Taliban was open to reconciliation, despite its pledge to continue its 'sacred jihad' against NATO and U.S. soldiers.
"The question has been to the Taliban, 'You have got a choice to make. Life's moving on," the second U.S. official said. "There's a substantial military campaign out there that will continue to do you substantial damage ... Are you prepared to go forward with some kind of reconciliation process?"
U.S. officials have met with Tayeb Agha, who was a secretary to Mullah Omar, and they have held one meeting arranged by Pakistan with Ibrahim Haqqani, a brother of the Haqqani network's founder. They have not shut the door to further meetings with the Haqqani group, which is blamed for a brazen attack this fall on the U.S. embassy in Kabul and which senior U.S. officials link closely to Pakistan's intelligence agency.
U.S. officials say they have kept Karzai informed of the process and have met with him before and after each encounter, but they declined to confirm whether representatives of his government are present at those meetings.