Re: Does my caller ID show up while roaming in Canada and making a call to the US?
In general, it should work, but there are no guarantees. There's always the possibility of the caller id getting lost somewhere along the way, but it should usually work from Canada - from other countries it'll be less reliable. I would expect either the correct number, or "out of area/unavailable". Now, if you're calling a toll free number they will probably get a number that identifies where you are calling from, rather than your own, because they use that for billing purposes (the owner of the toll free number would need to get charged for a call to Canada).