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Looking at my usage history, I think I did use up the add-on data already and there was just some sort of bug in the reported status of the add-on.

I wish I had taken a screenshot. Shortly after I opened a support ticket, my 1GB add-on with 0.93GB remaining and 0.0% used, totally disappeared from the add-on usage section of my plan and add-ons page. 

Cool, thanks, all. I've noticed that when I buy 1 GB of US roaming data, I get a ballance of 1 GB of US data left in my add-on usage page, but the last couple of times that I bought a 1 GB add-on of regular Canadian data I only got 0.93 GB (0.0% used...