A man thought to have carried out over 100 burglaries is seeking up to £15,000 from the Home Office for injured feelings.
Keith Bramble is up for parole in December 2004
Keith Bramble was jailed for a record 27 years in 1995.
But the 45-year-old claims his human rights were violated in prison and that he suffered racial discrimination.
London's High Court on Tuesday rejected Bramble's race claim but gave him six weeks to reformulate the rights claim. The Home Office denies the allegations.
Among Bramble's complaints are a failure to transfer his frozen food when he changed prisons and being segregated.
During his trial at Middlesex Crown Court in December 1995, the jury was told that Bramble believed he was evil.
He had armed himself with weapons including crowbars, knives and a screwdriver while committing his crimes, and also wore dark clothes and a highwayman's mask.
On sentencing, Judge Clarkson QC said that Bramble gloried in the terror he caused his wealthy victims, and that his crimes were more serious than raids on banks or building societies.
He sentenced him to 27 years - the longest term of imprisonment ever passed for domestic break-ins.
But the burglar, who is up for parole in December, is claiming damages for injury to his feelings, citing the Race Relations Act and the Human Rights Act.
Representing himself in the High Court on Tuesday, Bramble contested a bid by the Home Office to "strike out" his claim.
Bramble claimed that he had been racially discriminated against between July 1999 and September 2002.
He alleged a delay in passing on clothes sent by his partner, the removal of papers from his cell and a failure to transfer his frozen food from Long Lartin prison in Worcestershire to Whitemoor, Cambridgeshire, where he is now held.
Bramble also claimed that his human rights were breached by his segregation in prison - which he said exposed him to risk - and also by his genitalia being videoed during a strip search while female officers were within view.
The Home Office said that the racial discrimination claim was brought outside the legal time frame and that the human rights element was imprecise.
Judge Knight QC rejected his race claim on the basis that there was no essential connection between the allegations and racial discrimination.
He was also not satisfied that the case as put amounted to a breach of human rights.
But Judge Knight said that he would not throw the case out completely and would allow Bramble six weeks to reformulate his claim in writing.
A decision on who should pay the near £3,000 costs of the proceedings, which started in May last year, was reserved to a later date.