The city will be in a legal lockout position on February 27th, when it comes to their labour dispute with CUPE local 416, and the city "inside workers."
But on Tuesday, NEWSTALK 1010 was able to get a better idea of what are some of the sticking points in this back-and-forth.
And some, are pretty eyebrow raising.
"One is erectile dysfunction drugs, and we'd like to get some goal posts and some limits around that," says Deputy Mayor Denzil Minnan-Wong.
City employees have been charging their pills to the city, and it's costing almost $2 million a year.
The data was recently outlined by the City's Auditor General who also pointed out a couple of other areas of concern.
"If you work for the city, your kids can get an unlimited amount of orthotics," points out Minnan-Wong. "And that costs about $1.3 million."
He points out specific examples, where 41 dependents under the age of 18, claimed between six and ten pairs of orthotics in a year, worth between $3,000 and $5,000.
Another issue is the use of half-day sick days.
Believe it or not, city employees can take a half day, and it doesn't count to the sick day totals. Minnan-Wong wants to change that.
"We think that if you're taking some time off, then that should come from your sick bank."
The number of half-day sick days for members of CUPE local 416 has gone up 39% since 2016, and for members of CUPE local 79 and the inside workers, the number has jumped by 18% since 2016.
The Deputy Mayor also brings up another contentious issue; jobs-for-life.
"The union wants to go backward and they are still fighting to get jobs for life," says Minnan-Wong. "We think that the current arrangements are quite suitable and that these jobs-for-life should be limited."
Right now, city workers with 15 years seniority are covered by the provision, where they can't be fired if the city contracts out their jobs. The city would like to keep it that way.