A young American living in Australia used the Google Translate service in an attempt to contact Arabic-speaking Islamic State recruiters, according to US prosecutors.
Asher Khan, 21, faces life in prison if convicted at a trial in the US District Court in Texas in September.
Khan moved from Houston to Sydney in 2013 to live with relatives and while in Australia allegedly hatched a plan to fly to Turkey and cross into Syria to fight for IS.
Prosecutors revealed in a new pre-trial court filing authorities have forensically examined Google searches, Skype Chat messaging and other applications on Khan's iPhone and computer.
"I want to join the jihad, but I live in Australia?" Khan allegedly typed into Google Translate.
News that makes sense
Your trusted source for staying up-to-date with the world around you. Get free daily news updates and analysis, straight to your inbox.
"How can I come? I don't speak Arabic, only english and urdu (sic)."
Khan faces multiple charges with alleged Australian IS recruiter, Mohamed Zuhbi, including conspiring to provide material support to IS and conspiring to commit murder in a foreign country.
Zuhbi, 25, formerly of Sydney, was operating out of Syria and Turkey and provided Khan with "logistical advice" and a Turkish mobile number to call once he landed in Turkey, according to the indictment.
Khan allegedly flew from Sydney to Turkey, via Malaysia, on February 24, 2014, while his Texan friend, Sixto Ramiro Garcia, flew from Houston to Turkey a day earlier.
Khan was arrested in the US after his family allegedly tricked him into returning to Houston with a false story his mother was in hospital.
Garcia allegedly communicated with Khan that Zuhbi had "delivered" him and he had attended fighter training camps, but on December 25, 2014, Garcia's mother "received a message explaining that her son had died, suggesting that he died while fighting".
Khan and Zuhbi are charged with: conspiracy to provide material support to a foreign terrorist organisation; conspiracy to commit murder in a foreign country; conspiracy to provide material support to terrorists; and providing material support to a designated foreign terrorist organisation.
Khan has entered not guilty pleas, while prosecutors said Zuhbi is believed to be living "somewhere along the border of Turkey and Syria".
