Resumption of the process, which is simulcast from Cuba to a room at the Pentagon, came as a surprise given previous criticism by President Donald Trump of the Periodic Review Board, which Obama set up by executive order.
Trump was still president-elect on Jan. 3 when he said on Twitter that all Obama prisoner releases should stop.
"These are extremely dangerous people and should not be allowed back onto the battlefield," the tweet stated.
Falling short of his promise to shutter the military detention center before he left office, Obama managed to transfer nearly all of the detainees cleared for release after a last-minute transfer of 10 prisoners to Oman on Jan. 17.
That leaves 41 prisoners at the detention center.
The Pentagon has so far been mum on the future of the parole-board process.
Department of Defense spokesperson Maj. Benjamin Sakrisson said the Pentagon has no information yet on plans to release five detainees previously cleared for release who did not make it out before the change in administrations.
It is also unclear if Omar Mohammed Ali al-Rammah, who had his parole hearing Thursday morning, will be released if the board decides he no longer poses a national-security threat.
The Yemeni’s hearing was identical to proceedings under the Obama administration, complete with technical difficulties that jumbled the video stream shown to reporters and nongovernmental organizations at the Pentagon.
Unlike previous detainees, however, al-Rammah wore a blue T-shirt with black short sleeves. Most detainees come to their parole hearings in plain white shirts. Al-Rammah, who goes by the nickname Zakaria, appeared to have a gray, long-sleeved shirt on underneath his tee.
According to his revised unclassified profile, al-Rammah has been held at Guantanamo without charge or trial since his arrival in May 2003.
The U.S. believes Zakaria was a low-level fighter in Bosnia before he allegedly became a facilitator for al-Qaida affiliated extremists. Al-Rammah also "may have" trained in Afghanistan at camps associated with al-Qaida. That's before he apparently went to Georgia in 2001 to support the Chechen separatist movement.
Beth Jacob, an attorney for the detainee with Kelley Drye's New York office, painted a different picture, telling the board that al-Rammah never engaged in hostile actions against the United States. Al-Rammah, whom his family knows as Faisal, was a low-level gopher in Bosnia and Chechnya, Jacob said.
An anonymous personal military representative for al-Rammah made sure to say that the detainee is no radical.
"Zakaria is a moderate Muslim who denounces violence, death and destruction caused by radicals," the blond woman told the parole board, reading from a statement. "He enjoys Western movies, sports and video games.”
The representative and Jacob both described al-Rammah as well-behaved.
Though al-Rammah did participate in a hunger strike in the prison, Jacob insisted the strike was not political. She said al-Rammah had a crush on a nurse, and his participation in the strike was a clever ploy to see her.
Video of the hearing never shows the board or captures its members’ reactions, but Jacob’s description of al-Rammah’s romantic efforts drew laughter from several at the Pentagon watching the broadcast – a rare occurrence for periodic-review board hearings.
Turning to darker themes, Jacob said the trauma of his capture still plagues al-Rammah. Al-Rammah had never seen someone killed before his cab driver died during the raid, she said.
President Trump has yet to clarify what he will do with the detention center at the Guantanamo Bay Naval Base.
On Wednesday, The New York Times reported that a draft executive order indicates the prison will remain open, allowing President Trump to deliver on his campaign promise to fill it up with "bad dudes."
The draft apparently dropped language that would have revived the use of secret CIA prisons, but it says that Islamic State fighters could be sent to the prison.
Read the Top 8
Sign up for the Top 8, a roundup of the day's top stories delivered directly to your inbox Monday through Friday.