Whenever I click on a number like 1-866-555-4226, Skype pops up and says it will call an United States number +1-866-555-4226.
WRONG! It's a Canadian number, I'm in Canada, my country code is +1. How do I get Skype to be a little less brain-dead about Canadian country codes?
Actually Canada's country code is 011 + 1 + City Area Code + Prefix + Subfix in the skype setup page enter something like +011 5145551212 (montreal listing info)
Actually, Canada's counrtry code is 1, and is dialed as +1 via Skype. It's the same for the U.S. 011 is used to make International calls via a traditional landline but not via Skype.
I don't know if there's a solution for the problem the orignal poster had 9 months ago, but dialing 011 isn't it.