The closure of Guantanamo Bay prison will not be an easy one with many diverse prisoners from die-hard jihadists to innocent men swept up in war.
On Monday two presidential transition team advisers said that Obama is preparing to issue an executive order in his first day or week in office setting in motion the extensive survey needed to close the U.S. military prison in Cuba.
His team faces a daunting task. Some cases are very clear and decisive but others are unfortunately not the as clear.
The case of Khalid Sheikh Mohammed, is an example of a clear case. He was brought to Guantanamo in 2006 after being in Central Intelligence Agency custody and has claimed responsibility for the Sept. 11 attacks. He said he wants to be executed to achieve martyrdom.
At the other end of the spectrum are men even the Pentagon acknowledges are no threat - 17 Uighur dissidents who remain detained over fears for their safety if returned to their homeland in China.
The majority of the approximately 250 remaining prisoners lie in-between.
According to reports, Obama expressed the unlikelihood of the detention facility being closed anytime soon.
Obama was also reported as stressing that he will definitely close Guantanamo and that he would ensure the procedures to apply to the prisoners are ones that abide to the constitution.
The Guantanamo directive would be one of a series of executive orders Obama is planning to issue shortly after he takes office next Tuesday.
Many detainees have insisted on their innocence and have pleaded to be set free.
The Pentagon says about 520 men have been sent away from Guantanamo since it opened.