Is anyone else being denied the stopover program when flying from an American city to a Canadian city with a connection in YYZ?
Quote of the rules from AC web page...
"You’ll be offered the Air Canada Stopover option when you purchase a one-way or round-trip ticket (any fare) at aircanada.com or through your travel agent, provided:
You complete your booking at least 96 hours before your flight’s scheduled departure time.
You’re travelling on an Air Canada-coded flight operated by Air Canada or Air Canada Rouge, or an Air Canada Express flight operated by Jazz, Sky Regional, Air Georgian Ltd. or Exploits Valley Air Services Ltd.
Your itinerary includes at least one city outside Canada or the U.S. as well as a connection in Toronto, Montréal or Vancouver of over 6 hours"
We are flying SRQ-YSB on rouge and Express with greater than 6 hour layover in YYZ booked through AE, so we meet all the requirements. AC call centre can not correct the problem.

Your itinerary doesn't include at least one city outside Canada or the US...

SRQ=Sarasota, FL which is outside Canada but not outside the US. The rule reads a city outside of Canada OR outside of the US (not both) not outside of Canada AND the US.
We have used this program for the last few years on this same route.

That rule doesn' really make sense. I challenge anyone to name a city that isn't outside Canada or the US. Hint, Sault Ste Marie is 2 cities.

I thought it was well understood that this was a program for international itineraries, but if you want to get really pedantic...

"or" means "union". The set of cities in Canada in a union with the set of cities in the US is a set of all cities in both countries.

The rule says you need a city not in this set. All your cities are in that set. Therefore you are not eligible.

At least that's how I'd read it.

If you say you've been offered this on purely North American itineraries before, then I don't know what to say. I never have been.

Toronto, Ontario, Canada isn't outside (Canada or the US).

ie: Brazil to Germany on AC, stopover in Toronto, yes. Program is good. One can build for a day of meetings in Toronto or weekend departure and take a break while traveling between two continents while connecting in Canada.

But I think it is outside the US.

It is. But nowhere in the terms does the phrase "outside the US" appear. You'd have to remove a couple words to find that, which would DEFINITELY change the meaning.

It's not "outside Canada or outside the US" (as every city would meet that requirement). It's "outside Canada or the US".

You said you booked through Aeroplan, which is not aircanada.com or your travel agent.

If you have been successful at getting this before, then I think you have been lucky as the intent of this programme as I understand it is not for US-Canada itineraries.

Definition of 'and'... "used to join two words, phrases, parts of sentences, or related statements together"
Definition of 'or'..."used to link alternatives."
Definition of 'alternative'... "offering a choice between two or more things"
My understanding is 'or' is one or the other and not both. Using 'and' means both ie all cities in Canada and the USA. So using 'or' means you need a condition to satisfy one of the conditions not both.
Yes, we have used this program while flying from SRQ to YSB.
I dug up an old thread and the old wording was "and" but this wording is using "or".
D582 we have used this program when booking through AE for international flights as well. So I guess AC considers AE the equivalent of a travel agent.

The language is ambiguous - my contract law references use this sort of example to point out how NOT to write legal language. When it comes to legal language grammatical context makes all the difference in applying algebraic of digital-logic type TRUTH tests.

Google (you should be able to find this online):
"REVISITING THE AMBIGUITY OF “AND” AND “OR” IN LEGAL DRAFTING", KENNETH A. ADAMS & ALAN S. KAYE.

It isn't the use of "or" or "and" that is the issue - it is the construction.

The text above would advise a lawyer to write out a construction such as this with all its possible interpretations, there is at least 3 for the way the phrase is currently written, although two are probably non-sensical given what was intended, they still point out the ambiguity. The phrase needs to be written to be clear where the "outside of ... or" test applies, either collectively or separately and whether it is logically a "OR" or "NOR" construction.