Manchester Magistrates' Court heard Stephen Andreassen, 38, compiled up to 35 website blogs in which he repeatedly insulted an ex-girlfriend after she ended their month-long relationship.
Over 18 months Andreassen regularly updated his sites telling men to stay away from mature university student Rebecca Pattinson, 36, while bombarding her with Facebook messages, texts, phone calls and e-mails begging for her to take him back.
On one occasion, Andreassen posted her a copy of the Harper Lee novel 'To Kill A Mockingbird' with a note deliberately inserted in a chapter in which the main character, Atticus Finch, tells his children what rape is.
Andreassen, who was sentenced to 18 weeks, had twice previously been hauled to court over his online hate campaign against Pattinson and was issued with a restraining order.
However, he continued his campaign, which included sending messages to her family in an attempt to turn them against her. When his tactics failed, he booked himself into a hotel and took numerous pills in a suicide attempt, which he had foreshadowed in a blog.
"The longer you refuse to speak to me, the longer this goes on and on. I'm not the monster you've built up in your mind," the Daily Mail quoted him as having written.
"What exactly did I do that you feel you can never talk to me again? I'm pretty sure I would have remembered murdering someone.
"I've given up making sensible requests, so here's my latest... Meet me for 3 minutes, anywhere you want. You only need to stay and talk for as long as I refrain from punching a nun or eating a live otter. It's already beyond ridiculous," he wrote.
Andreassen boasted of being so skilled in IT he could set up new offensive blogs about Pattinson quicker than they could be deleted.
Last year Andreassen, of Urmston, Greater Manchester, escaped jail but was banned under a lifetime restraining order from mentioning Pattinson on any websites after he admitted harassment.
Yet two months later he was arrested again after he posted another entry on his blog detailing the court case and called the woman involved a "liar" and "a sociopath".
He was spared jail again but he set up a new obsessive website with various pages including sections labelled 'The Relationship', 'My Story' and 'Court appearance'.
The ordeal left Pattinson behind in college coursework and she was prescribed anti-depressants as well as given counselling.
"The whole situation has been extremely stressful. I've been feeling distressed by Stephen's actions and feel unable to cope. I can't stop him from doing this," she wrote in a statement.
"It breaks my heart that not only has he done this to me but he has dragged my family into it also. I fear that Stephen will never stop and I can't understand why he is doing this," she stated.
In what is thought to be the first case of its kind Andreassen, who has since been fired by NHS Manchester, was jailed for 18 weeks after he admitted breach of a restraining order.
"Mr Andreassen felt it was important to get his side out there," in court, defence lawyer Tim McArdle said.
"He didn't draw attention to the site, or publicise it, and had someone not been looking for it they wouldn't have found it.
"He attempted suicide not as a cry for help, but as a desperate act," he stated.
Magistrates ordered Andreassen to take the website down.
"We have decided that this does warrant custody, and we are going to activate the suspended sentence served on you," they added.