On July 20, 2002, two dozen American Special Armed Forces soldiers, acting on an anonymous tip, raided Obaidullah's family home and took him into custody along with his cousins.

At the time, Obaidullah was carrying a notebook which the U.S. alleges contained diagrams for improvised explosive devices.

[12] In a statement made during his habeas corpus proceedings, Obaidullah stated: The Americans came while my family and I were all sleeping in our home in the village of Milani, close to Khost City.

Obaidullah described his treatment at Chapman airbase in a statement made during his habeas corpus proceedings: After I got to the military base, there were several soldiers who told me to put my hands up and then to hold them straight out to the front of me.

When they moved me from one location to another, the soldiers were extremely rough and shoved me around with their knees and elbows in a very painful and frightening way.

[13]Obaidullah reported abusive interrogation while held in Bagram, during a period when the officers in charge have acknowledged directing the use of the proscribed technique of chaining a detainee's hands above his head in order to impose sleep deprivation.

According to Obaidullah, he joined a hunger strike spurred by "invasive" cell searches conducted in February 2013.

[13]Originally, the Bush Presidency asserted that captives apprehended in the "war on terror" were not covered by the Geneva Conventions, and could be held indefinitely, without charge, and without an open and transparent review of the justifications for their detention.

Following the Supreme Court's ruling the Department of Defense set up the Office for the Administrative Review of Detained Enemy Combatants.

[17][20] Scholars at the Brookings Institution, led by Benjamin Wittes, listed the captives still held in Guantanamo in December 2008, according to whether their detention was justified by certain common allegations:[21] Obaidullah testified at his 2004 and 2005 hearings.

[22][23] Following the U.S. Supreme Court's ruling in Boumediene v. Bush that Guantanamo detainees are entitled to habeas corpus proceedings, Obaidullah filed a petition for habeas corpus in the U.S. District Court for the District of Columbia in July 2008.

[25] Judge Leon denied Obaidullah's petition for writ of habeas corpus after finding he was "more likely than not" an insurgent.

[27] "Individuals who had lived in Obaidullah's village identified two males who were not originally from the same village but had lived there for a period, and who were rumoured to have sold false information to Americans," a Navy intelligence officer investigating Obaidullah's case in Afghanistan said in a sworn statement.

This evidence was attested to in a declaration by Lieutenant Commander Richard Pandis, an NCIS investigator assigned to the case.

[29] On April 25, 2011, whistleblower organization WikiLeaks published formerly secret assessments drafted by Joint Task Force Guantanamo analysts.

When he assumed office in January 2009 President Barack Obama made a number of promises about the future of Guantanamo.

[36] When it reported back, a year later, the Joint Review Task Force classified some individuals as too dangerous to be transferred from Guantanamo, even though there was no evidence to justify laying charges against them.

On September 10, 2008, charges were filed against Obaidullah for "conspiracy" and "providing material support for terrorism" under the Military Commissions Act of 2006.

[38][39] According to Reuters: Anne Richardson, one of his lawyers, described how, when his defense team were able to disprove the allegations used to justify detaining him, and on which the charges he faced were based, the prosecution chose to drop the charges, instead of allowing him to prove his innocence, at trial, which would have justified freeing him.

Obaidullah appears on a Department Defense list of "71 Guantanamo Detainees Determined Eligible to Receive a Periodic Review Board as of April 19, 2014.

[44] On August 15, 2016, the USA transferred Obaidullah, and fourteen other men, to the United Arab Emirates.

[9] The Independent noted that Obaidullah had maintained he was tortured into the confessions that led to him being charged, and that he was assessed not to hold anti-American feelings.