The man set up an account on a microblogging social media website under the name "wanderingphilosopher", through which he claimed to be "into everything and anything twisted ... Looking forward to conversing with the like-minded sick freaks on here".
Over two years, Whitcombe was involved in 17 exchanges in which he expressed a desire to rape babies and discussed other objectionable matters.
Some conversations were so graphic, court documents had to be redacted.
An investigation by Customs showed Whitcombe had also downloaded child-abuse material at a North Dunedin address and his parents' home.
When his house was raided, he admitted he knew the files he had were "bad" and that he had used an app since he was 14 to communicate with people around the world.
The Parole Board noted Whitcombe had a hefty student loan, accumulated over four years of studying philosophy.
Whitcombe's pursuit of education had continued behind bars.
Panel convener Judge Neil MacLean said Whitcombe was now studying accounting and was undertaking some cooking lessons while at the Otago Corrections Facility.
Whitcombe will appear before the board again in September 2020.
