Neil Johnson, 38, was made the subject of a 10-year Sexual Harm Prevention Order (SHPO) after he was dealt with for indecent images of children in May 2019.
It includes a number of conditions to regulate his use of devices with internet access and for police to check them.
But Teesside Crown Court heard Johnson has an ongoing attraction to children and breached the order six times.
When police went to his house in June last year to inspect a new laptop he had bought, a number of homemade DVDs featuring images of naked or partially naked children were found.
There were 53 similar pictures on the laptop that while not illegal breached the order.
The court heard he set up two accounts on the computer to help hide what he was doing from his family.
Johnson also did not tell police about a USB memory device he had and admitted deleting some of his internet history when he made searches with the word “kids” in them.
While on police and court bail, he committed further breaches in April this year by deleting the internet history on his Xbox games console and setting up a linked email address with someone else’s name.
Anthony Pettengell, defending, said Johnson, of Park Road, Hartlepool, who has autism, had tried to stick to the order and asked to be banned from owning a laptop.
Jailing him for 20 months, Judge James Brown said: “Sadly, this collection of offences is so serious that only an immediate term of custody can be imposed.”