The big disconnect: Air Canada and Aeroplan have big issues after system update
We reported earlier in November that Air Canada was going offline for a few days while it updated its system. Unfortunately, while that update is complete, booking issues remain rife between Air Canada and Aeroplan, the operator that handles its award bookings. As noted by Live and Lets Fly, the system is currently unusable and any attempts to book award tickets fail completely.
TPG's own tests to book a ticket failed as well, confirming the seeming disconnect between Air Canada's new backend system, Amadeus and the processes that Aeroplan uses in order to ticket awards. From Aeroplan's website, customers entering itineraries and searching for availability receive this message:

The above error message occurs regardless of city pairs/dates/cabin entered. In this case, a search was performed for a one-way ticket from Toronto (YYZ) to New York (JFK). When searched on Air Canada's own website, however, availability is both plentiful and cheap:

Clearly the issue is somewhere between the two providers, and it's been this way since the migration. Other users are also reporting the ability to see and attempt to book an award ticket, with a final failure occurring when attempting to make a purchase.
It's always a risk when multiple companies handle a situation, especially when they need to rely on each other in order to work. In this case, Aeroplan, the award program of Air Canada, needs access to Air Canada's backend system in order to successfully offer and ticket award bookings. Unfortunately, Air Canada's updated system appears to have broken this link, at least for now.
While it's a shame that customers are unable to book new tickets this is hopefully something that Aeroplan and Air Canada will sort out soon, especially with upcoming holiday travel.
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