No, in this case they were not theoretically flyable. On the same day, I was scheduled to do:

• PNR 1: YYC-YKA-YYC
• PNR 2: YYC-YYJ-YYC
• PNR 3: YYC-YVR
• PNR 4: YVR-YEG-YVR
• PNR 5: YVR-YYC

I was either going to do (a) PNRs 1 and 2 or (b) PNRs 3, 4, and 5.

PNRs 1 and 2 both overlapped with PNR 4. PNR 2 might also have overlapped with PNR 5. PNR 2 was flagged by Amadeus as duplicate with PNR 4 and cancelled. No other PNRs were flagged.

Now, that being said, it has in the past flagged non-conflicting bookings as duplicates, and cancelled one. For instance, I had YUL-YYC bookings on both the 18th and 19th (evening and morning, respectively). The booking for the 19th was flagged as duplicate and cancelled, even though one could fly the one on the 18th, take the YYC-YUL redeye (or perhaps a YYC-YYZ-YUL) and make a legal connection to that one on the 19th.

I got the one for the 19th re-booked after concierge talked to the FP people, but it got auto-cancelled again. So when I re-booked it for the second time, I also booked the redeye in between. So far, that 3rd booking for the 19th has stayed in place. I'm not sure whether booking the redeye has convinced the system that it's not a duplicate or it just hasn't gotten around to cancelling it yet.

I think FPs are a particular problem here. A helpful concierge I spoke to the other day said that there should be an e-mail generated by the system that flags these issues for the traveller and gives them warning that a booking will be cancelled. And from some reports upthread, I think that may happen, at least sometimes. But I'm now up to about 6-8 cases of this and have never once received any advance warning. There's also nothing when the booking gets cancelled; the PNR just ceases to be (it expires and goes to meet its maker, etc). He did say he would flag that to the FP and IT teams, but I don't know whether that will go anywhere.

I'm also not sure how useful that warning would be. When I had that concierge working with me on this the other night and we re-booked the YYJ flight, as soon as I booked it (new PNR), he saw a flag on the PNR about auto-cancellation, so Amadeus detected it right away. The warning said that it was going to be cancelled at a time that was only about 3 hours away from when we made that booking. If AC sends me a warning at 2AM that I need to change or cancel something by 5AM, I'm likely not going to have any chance to take action on that. Then again, some of those other bookings existed for over 24 hours before getting cancelled, and when he dug through the notes on one of the PNRs, it looked like it had given a lot longer period (I don't remember exactly how long) to resolve the conflict.

At some point I need to make some totally dummy bookings on days when I have no intention of flying, and carefully monitor when I book them and when they get cancelled. I'll also try to get the concierge to tell me exactly what the note says.

But I've spent enough time on this nonsense in the past few days, that will have to wait a bit.