The troubled star, 25, admitted that she violated her probation terms by stealing a gold necklace.
But her lawyer bargained with the LA Superior Court to delay her prison sentence by a week, so she could do the racy photo shoot.
The judge agreed to let her fulfil her $1million contract for the photos on the condition that she reports for jail next Wednesday.
The Mean Girls actress will appear on the front cover of either the December or January issue of Hugh Hefner’s magazine, it is rumoured.
But sherriff’s officials say Lohan may only serve a few hours due to prison overcrowding.
When she is released, Lohan will have to do five months’ community service, which will include sessions at the county morgue.
She will also be forced to attend psychotherapy sessions and appear at monthly court hearings from December to March.
The star’s legal problems began in 2007 when she was caught driving drunk.
That year, she spent 84 minutes in prison before she was released.