Weird bumping into another Canadian on here!
I am not on the Trillium plan but it was my understanding this plan covers 3000 test strips per year. Which would be 30 box, which is just over 2 per month.
I have run into pharmacies that require you to wait 2 weeks before you can refill a prescription - which means you can't walk in once a month and get 2 boxes, you'd have to go every 2 weeks or so that their system allows the re-fill.
I would try other pharmacies just to be sure. Ask for more detail if someone tells you they 'can't do that'