Originally Posted by
canfly15
I learned something useful the other day. I planned to travel from YYJ to YYZ using an upgraded Latitude pass and get a companion Executive class Aeroplan points ticket for Mrs Canfly15. There seemed to be plenty of open seats at the front and it showed availability for immediate upgrade. Being a (sort of) gentleman, I booked my wife's seat first and there was no problem. But when I then went to get my ticket, it said I would have to be wailtlisted for the upgrade. I guess her points ticket used up the space available for immediate upgrade.
So the lesson appears to be: buy the ticket first to grab the upgrade and then get the points ticket next because SE priority awards should make that available. Moral of the story: it does not always pay to be a gentleman!
I have had this issue before too.
Unfortunately, this seems to work both ways. Would you have booked your upgrade, the Aeroplan availability might well have disappeared.
At the end of the day, it's still is probably better to start with the reward, because your upgrade on a Latitude fare still likely will end up confirmed. When I had the same problem, another R seat appeared quickly after and I grabbed it.
But best is to check first if the R inventory is at least two seats. Do a mock booking for two, you'll see that.