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US District Judge James Zagel in Chicago said Khan displayed "toxic altruism" while sentencing him to 90-months in prison followed by lifetime supervised release.
In addition, the judge said it was a "profoundly aggravating factor" that Khan's crime occurred after he voluntarily chose to become a naturalised US citizen.
Although Khan's actual donations of approximately $500 to $550 and attempted donation of $1,000 were not incredibly substantial amounts, donations need not be large to be of assistance to terrorist organisations, the government argued, and the judge noted as well.
Khan, who was born and resided in Pakistan occupied Kashmir before immigrating to the US in late 1970s, admitted that he met Kashmiri in Pakistan in the early to mid-2000s and again in 2008.
At the time of his second meeting, he knew that Kashmiri was working with the Al Qaeda, in addition to leading attacks against the Indian government in Kashmir, a US justice department statement said.
During their 2008 meeting, Kashmiri told Khan that Osama bin Laden was "alive, healthy, and giving orders," and he gave Kashmiri approximately 20,000 Pakistani rupees, which he intended Kashmiri to use to support attacks against India.
On November 23, 2009, Khan sent approximately Rs 77,917 from Chicago to an individual in Pakistan and directed him over to give Kashmiri approximately Rs 25,000.
Although Khan intended the funds to be used by Kashmiri to support attacks against India, he was also aware that Kashmiri was working with the Al Qaeda.
According to the Department of Justice, in February and March 2010, Khan participated in several meetings with an undercover law enforcement agent who posed as someone
interested in sending money to Kashmiri to purchase weapons and ammunition, but only if Kashmiri was working with Al Qaeda, as well as sending individuals into Pakistan to receive military-style training so they could conduct attacks against US forces and interests.
On March 17, 2010, the undercover agent provided Khan with $1,000, which Khan agreed to provide to Kashmiri. Khan then gave the funds to his son, who was traveling from the US to the United Kingdom, intending to later retrieve the money from his son in the UK and subsequently provide it to Kashmiri in Pakistan.
On March 23, 2010, Khan's son arrived at an airport in the UK and a search by the law enforcement officials yielded seven of the 10 $100 bills that the undercover agent had provided to Khan.
After learning of his son's detention, Khan attempted to end his involvement in the scheme to provide funds to Kashmiri by requesting an urgent meeting with another individual who was also present at Khan's earlier meetings with the undercover agent.
During their meeting, Khan demanded to return the undercover agent's funds by providing $800 to this other individual.
Khan's plea agreement called for an agreed sentence of between five and eight years in prison, and it requires Khan to cooperate with the government in any matter in which he is called upon to assist through the termination of his sentence and any period of supervised release.