Hey, in order to get Cortana functional in your region, you must go to settings (via Win Key + "I"), then click on "Time & language", and then click on "Region & language". Once you're there, under "languages', you will see the language packs installed on your machine. For instance, in your case, you will see: "English (Canada)", and English (United States)". Furthermore, click on "English (Canada)", and then click on "options". Once your inside, windows update will automatically, or if not, prompt you to install the speech/voice add-on for your windows display language.
P.S: Oh by the way, in the latest windows insider preview build (10547), Cortana for Canada is currently dysfunctional at the moment. It seems that the latest build has ruptured/broken the feature; thus, you will need to wait until the next build, or until they patch and send out a fix via Windows Update.
09-25-2015 01:01 AM