A serial sex offender banned from contacting women bombarded a support worker with nuisance calls over a two-month period.
Ian King, 34, made the woman fear for safety in her role with social care charity Turning Point between January 29 and March 8.
King is subject to a sexual offences prevention order, imposed in 2013, which limits his contact with women.
The creep has now been jailed after he admitted at Dundee Sheriff Court to breaching the order for the 10th time in eight years.
Sheriff Alison Michie said: “Your record for analogous offending in the same way is truly horrendous.”
The court heard how King, who has learning difficulties, was receiving support from Turning Point during this period.
On one occasion, he asked the woman to attend at his flat to set-up a new alarm clock but became “hostile” when a male employee was sent.
Fiscal depute Emma Farmer said: “The complainer had contacted the police due to the extent of the nuisance calls to her and her office.
“The accused’s mobile phone was seized for further examination.
“On March 6, the accused requested that the complainer and other staff attend his flat to set up a new alarm clock radio he had purchased.
“A male member of staff attended alone, at which point, the accused became hostile and no longer wished assistance.”
King, of Kirk Street, Dundee, would repeatedly call the woman’s office and hang-up the phone when another staff member would answer.
Police again spoke with King who said he was sexually attracted to the woman.
An assessment was carried out and it was determined that he posed a high risk to her.
Ms Farmer added: “The complainer advised that the actions of the accused had made her feel uncomfortable and unsafe at work.
“She said the accused’s repeated contact to her made her fear for her safety.”
King appeared from custody to plead guilty to breaching the terms of the order by unnecessarily contacting the woman by repeatedly phoning and messaging her as well as attending her office, approaching her, loitering and following her.
David Rogers, defending, said King was aware of the severity of the offence and could offer little mitigation to Sheriff Michie.
King was jailed for four months.