I assume you are booking these as two separate reservations. So how is expedia to know they are back to backs? It is processing each booking independent of the other, as it was likely programmed to do. It is only in the human audit process that things like this get caught. Obviously, expedia has not built in a sub-routine to detect such practices. I suspect you could book the same thing on AC's site and not get caught until the two separate bookings are linked by the commonality of your Aeroplan number. At that stage, AC may have a sub-routine that alerts their audit people, who would then manually investigate each booking.
The reason you'd have problems booking this through AC res with an agent is that s/he is there to monitor and act as auditor at the booking stage. Same with a travel agent. The TA may go ahead and make the bookings, on separate files and issuing separate tickets, then leave it to the airline to discover something may be amiss.
I would just be careful when calling AC to confirm any upgrades, and to it with a separate call for each itinerary. Also, you may find the audit process kicks in at the Aeroplan posting end. If the trips are tagged with their respective res numbers, and the posts look suspicious, your original bookings can be traced.
[This message has been edited by Shareholder (edited 08-28-2001).]