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Radical cleric Abu Qatada must remain behind bars until he leaves Britain after an immigration judge heard "jihadist files" were found on digital devices in his home.
Refusing the terror suspect bail, Mr Justice Irwin said a recent pledge by Qatada to voluntarily return to Jordan did not stop him from being a major flight risk.
Qatada was locked up in Belmarsh prison in March after breaching a bail condition which restricts use of mobile phones and other communications devices.
The Special Immigration Appeals Commission (Siac) heard that a USB stick understood to belong to Qatada's oldest son contained videos made by the "media wing of al Qaida".
Handing down his ruling, Mr Justice Irwin said:
"A serious matter relating to the breaches of bail was revealed during the hearing.
"In his witness statement, the appellant assured the Commission that nothing would be found on any of these items other than schoolwork or other innocent material.
"This assurance has proved untrue. Significant jihadist material has been found on a USB stick seized."
Earlier this month, it emerged the controversial preacher is willing to return to the Middle East when a treaty between the UK and Jordan is ratified by both countries.
The agreement, unveiled by Home Secretary Theresa May last month, aims to allay fears that evidence extracted through torture will be used against Qatada at a retrial.
Qatada's lawyer Daniel Friedman QC told the hearing that the treaty also "raises his prospects of acquittal in relation to what we say are tainted charges".
Mr Friedman argued that Qatada was a "proud and dignified man" who "has been deprived of his liberty more than any other non-convicted person in British history".
Mr Friedman added:
"He wants to spend time with his family to prepare to leave the country in a manner that safeguards the dignity and security of all involved."
Qatada admitted breached bail conditions which prevent him from turning on mobile phones and possessing other communication devices at his taxpayer-funded home in London.
Mr Friedman said Qatada accepts that six mobile phones belonging to his wife and his children could have been on but doubts they were on.
He added: "He didn't use them and didn't want to use them."
Robin Tam QC, who represents the Home Office, said £5,000 in cash was also found during the search of Qatada's property, although this was not a breach of bail.
Mr Tam said Siac itself had once described Qatada, also known as Omar Othman, as a "truly dangerous individual" and there was "no reason to believe that's no longer true".
Mr Tam said the family were not taking the bail order "seriously" and denied that items found in the house were "innocent".
The barrister also revealed that a USB stick found in Qatada's older son's room contained school work but also "jihadist files" including references to al Qaida.
With regards to the treaty, Mr Tam said the "parliamentary process will be completed within weeks".
He went on:
"At this time, Mr Othman definitively accepts he has lost his fight against deportation."
The Government has been trying to deport Qatada to Jordan, where he was convicted of terror charges in his absence in 1999, for around eight years.
At an earlier Siac hearing, Qatada's lawyer Edward Fitzgerald QC said his vow to return removed any risk that he would abscond if released on bail.
A total of 17 mobile phones, three USB sticks, one SD card, five digital media devices and 55 recordable CDs or DVDs were found.
Mr Justice Irwin said:
"This appellant has in the past fled in order to avoid a court order, equipping himself with a false passport.
"He is highly intelligent, has a range of sympathetic and supportive contacts, and his risk to national security is undiminished.
"We reject the submission that he can, even now, be relied on to comply with his legal obligations and not to attempt to abscond."
Qatada is also being investigated by Scotland Yard over suspected extremist material found during the search of his home.
The Metropolitan Police passed on the material to Danish authorities to reportedly investigate a connection with a controversial Islamic publisher.
Copenhagen Police said they had subsequently arrested a man, who is understood to be Said Mansour, a Moroccan-born Dane who was jailed for three-and-a-half years in 2007 for promoting terrorism.
Copenhagen's chief prosecutor Dorit Borgaard confirmed that the case concerns alleged encouragement of acts of terrorism.