Mark Ingleson, 52, had conversations of a sexual nature in WhatsApp messages with who he was told was a 14-year-old boy over six days January, Leeds Crown Court heard.
Ingleson, of Grange Court, Knottingley, arranged to meet the boy, the court was told.
Members of Paedophile Hunters - who had set up the fake online profile - then confronted Ingleson at his home address.
Paedophile Hunters contacted police and Ingleson was arrested.
Prosecutor, Martin Robertshaw said Ingleson had conversations of a sexual nature with a member of the group who was posing as a 14-year-old boy bewteen January 15 and 21.
Ingleson admitted his actions breached a sexual harm prevention order made at Leeds Crown Court on February 10 2017.
That five-year order was made after Ingleson was convicted of meeting a boy under 16 following sexual grooming and handed a suspended prison sentence.
The order banned Ingleson from having unsupervised contact with anyone aged under 16 and from using the internet to contact anyone under 16.
Mr Robertshaw said there were 19 pages of WhatsApp messages between Ingleson and the Paedophile Hunters in January.
Mr Robertshaw said: "The prosecution take the view this was a serious breach bearing in mind the number of ocasions this defendant was in contact with the fake person over the internet."
In June 2017, Ingleson was jailed for 19-months after he was convicted of meeting a boy under 16 plus two breaches of the sexual harm prevention order.
Mitigating, Kate Bisset said Ingleson has lost his job and is unemployed and socially isolated.
Miss Bisset added: “It was a terrible lack of judgement.”
Judge Mushtaq Khokhar jailed Ingleson for 16-months for breaching his sexual harm prevention order in January.