Originally Posted by JJonahJ

TD probably messed up the setup of your card when they took over control of your CIBC card. TD are still issuing Aeroplan Visa cards, and they are the initiial instigator to get the process started, so I would contact them. Mention that this is a card that has been in existence since 2014 and you've never (?) been able to get the Zone 2 and free luggage on the first try. You can't be the only one in this situation.

Just to be sure though, let's back up a step. Has your Aeroplan number changed since you applied for the CIBC card? If the Aero number that is linked to the card is not the same as the Aero account that was used to redeem for the flight reward, then there's that obvious disconnect.