South African police are searching for the first man to escape from the top security C-Max prison near Pretoria
Ananias Mathe, 29, from Mozambique, was detained last December on more than 50 charges, including murder, rape, armed robbery and hijacking.
He is reported to have escaped by covering his body in Vaseline and squeezing through his tiny cell window.
Police describe him as "the ultimate criminal" and were delighted to have caught him last year.
The window he escaped through on Saturday night is said to measure just 20cm by 60cm (8in by 2ft).
"It is alleged Mathe uncuffed himself, broke through a number of small windows and forced himself out on to the centre's roof - an escape carried out with military precision," said correctional services official Bheki Manzini.
He is also reported to have used the grime he was covered in to scrawl an offensive message on the wall he climbed down.
Correctional Services Minister Ngconde Balfour has called for an investigation into Mr Mathe's escape.
"I don't think that any offender can just escape as easy as that from C-Max. I know C-Max, I've been there several times. There must be some collusion that took place," he said.
Mr Mathe, who is said to have had extensive military training dating from Mozambique's civil war, first escaped from custody in April 2005.
"We are devastated. We have gathered the team and have regrouped. We will not sleep until we get him," said Captain Arnold Boonstra, the police investigating officer who was part of the team that first captured Mr Mathe.
He is the first person to escape from C-Max since it was built 36 years ago.
Border guards have been placed on high alert in case he tries to return to Mozambique.
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