Gerald Klein served three years in prison for the criminal harassment of Cathy Kaip. (CBC)

A Regina stalker who has habitually targeted the same woman for 35 years was due to leave the city Monday night or face arrest for violating a court order to stay away from her.

An unusual peace bond condition barring Gerald James Klein from living in Regina takes effect at midnight CST. For the next year, he is forbidden to enter the city limits unless it's for a medical emergency or to attend court.

'Gerry Klein has cast a dark cloud of anxiety and fear over the life of Cathy Kaip.'—Justice Larry Kyle

Klein, 63, was handed a peace bond in mid-August after a two-year-long battle by the Crown to obtain one over concerns for the safety of Cathy Kaip, a Regina woman who they say Klein has stalked for more than three decades.

Klein has been jailed in the past for criminally harassing Kaip.

He had sought to have the bond stayed while he appeals, but the courts denied that request.

Kaip said in a recent interview with CBC News that her experiences with Klein date back to 1974, when she met him at a wedding.

Many years of unwanted phone calls, letters, flowers and gifts followed. Kaip and members of her family were followed and harassed.

In 2006, a Saskatchewan judge's appraisal of Klein's harassing behaviour toward Kaip was read at a bail hearing.

"Gerry Klein has cast a dark cloud of anxiety and fear over the life of Cathy Kaip," Justice Larry Kyle wrote.

"Under the guise of what he has called love, a vengeful, controlling man has set out to harass and intimidate a woman who, from their very first meetings, made it clear that their relationship had no future," he stated.

Regina police said they won't be watching to make sure he leaves when he's supposed to. A spokesperson said, however, that if they receive a complaint that he hasn't left, they will investigate.

Klein's appeal of the peace bond will take place Oct. 21.