Sentencing for a serial fraudster found guilty of conning multiple Halifax-area businesses began on Tuesday.

The woman pleaded guilty to 19 counts stemming from nearly 50 charges involving fraud, forgery and impersonation.

She used so many aliases, even the court was at odds Tuesday over how to address her.

According to an agreement statement of facts, Alissa MacGillivary defrauded the Department of Community Services of just shy of $20,000 in income assistance payments over eight years.

It states she also applied for medical insurance under multiple false identities by forging birth certificates to receive payouts.

“I don’t think I’ve ever seen anything that had this many interweaving offences and this kind of complexity in terms of the offences,” Crown lawyer William Mathers said.

“For instance, using forged birth certificates to obtain Nova Scotia health cards for children that didn’t exist.”

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In 2020, MacGillivary got a job at Southland Transportation in Dartmouth and admits to falsely claiming she had a three-year-old daughter who was killed by a drunk driver in Newfoundland in order to obtain bereavement leave.

She later worked for Kent Building Supplies in Lower Sackville under a different name, claiming various family members had died and forging their death certificates to receive more than $5,000 in paid leave and an additional $3,000 fundraised by her co-workers.

“What the Crown is alleging here is that this individual spins endless narratives of victimhood, that she has learned that ordinary, decent people are … unwilling to question certain types of lies,” Mathers said.

In 2024, MacGillivary worked for Biships Cellar and Krown Rust in Halifax, using similar ruses to get paid leave before her eventual arrest.

But according to the defence, she is ready to make amends.

“She’s apologizing for her actions. She’s nowhere near proud of what has happened, so she is just at this place where she is ready to receive her sentence and get the help she needs,” said her defence lawyer, Carbo Kwan.

Born Katherine MacDougall, she legally changed her name to Alissa MacGillivary but has also gone by Alexandra Ryan and various other aliases for her fraudulent activity.

The prosecution and defence have opposing recommendations heading into sentencing. MacGillivary’s lawyer is suggesting a lesser custodial sentence of 3.5 years for the 19 charges she has pleaded guilty to, but the Crown is pushing for more.

“The Crown is seeking a custodial sentence of five years, less this individual’s remand credit,” Mathers said. “I worry that these kinds of offences do harm to genuinely vulnerable women and real victims.”

A decision on sentencing is scheduled for May 21.

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