I'm booked on AC34-AC194 for Wednesday April 20th. Waited until this morning 10:25 to request my eUpgrade online, so the 4X24 hour window. When my AC34 flight didn't become available for upgrade, I called AC Reservations. The agent on the phone was very nice but told me I can't request an upgrade until all my flights are available for upgrades, meaning I have to wait until 11:00 tomorrow.

For my incoming flight to SYD, I requested my upgrades for both segments separately, when the YUL-YVR segment opened, then the next day when the YVR-SYD segment opened.

Am I the only one to whom this has happened? It seems extremely penalising for such a long flight to wait until all segments are available for upgrade.

Is this a case of calling back AC until I get an agent who'll actually do it?

Online, you can upgrade from (for Elites) 96 hrs before each of the connecting flights - ie 96 hr before the first flight and 96 hrs before the second flight. Until Feb 28, 2011, when paper certificates were used for upgrades, one could upgrade all (connecting) flights, starting from 12:01 AM, 4 days before the flight.

Yes, that's how it's supposed to work, but OP is saying that (a) it didn't work for him and (b) AC Res agent said it was 96h before connecting flight (which hasn't been my experience, but jibes with OP's experience).

Yes that's how it does work. I logged on to try again just now. My YVR-YUL flight still isn't in the 96 hour upgrade window, but I was able to request an upgrade for the SYD-YVR segment.

Obviously waitlisted but still. Another case of the eUpgrade system not working

Under the new system, my understanding is that pax transiting through YYZ enroute to SYD will have the upgrade advantage since YYZ-YVR-SYD are a single flight number and can presumably be upgraded at the YYZ-YVR check-in window, whereas pax connecting on other flights to SYD via YVR will need to wait until the YVR-SYD window opens up. This is an assumption on my part rather than a fact, and in practice it may not matter much considering the popularity of this route and the fact that most upgrades will continue to be handled at the gate.

SG

My last upgraded flight I was able to upgrade online HKG-YVR right when window opened but not the YVR-YYC flight. When the window opened for that flight I upgraded it and was not charged additional eupgrade points as it was a connnection. System worked fine for me.

The old system had the same advantage.

People in YVR from continuing tickets on a single flight number are always left behind the 8 ball.

You are correct that YVR has always been last, but the field is much more level now (with the exception of the YYZ-YVR-SYD travelers).
In the old system, you could upgrade the entire itinerary when the window opened up for the first connection. LHR-YYZ-YVR-SYD could in theory snag the upgrade inventory on YVR-SYD prior to anyone in YYZ or YVR. Under the new system, each segment is treated as a single transaction. In practice many of these differences in the old system were evened out by allowing 12:01 a.m. upgrade at the 4 or 7 day window.

Under the new system, however, upgrade times are rigorously enforced. People flying from Vancouver are on an equal footing with everyone else EXCEPT for YYZ-SYD passengers travelling under a single flight number.

May not make any practical difference, but an interesting anomaly of the new system. Normally I would avoid the single flight number out of YYZ due to reduced status mileage, but e-upgrade potential is definitely a consideration.

SG

And EZE-SCL-YYZ

Had a similar (but different!) experience yesterday. Have Elite status, and am in syd with SYD-YVR fight at 10.25 on July 16. At 11.00 on July 12, still couldnt access eupgrade online. Phoned local resevations office who put me on the waitlist (which immediately showed up online)? Upgraded my connecting flight once it was in the 96hr window.

Can anyone definitively state when the upgrade window opens? Surely it should be automatic at 96hrs?

should be automatic 96 hours, but u never know if theres IT problem