playing devil's advocate here, you sure your colleague waitlisted after you? maybe he tricked you so he could upgrade first if there was only 1 seat ;)

AY, if you could confirm again that the waitlist gets transferred over at the 24 hour mark and checking in early doesn't cause you to go from the waitlist to airport list, we could attempt to try and figure it out while you sit back and have a good laugh at us trying to guess the trade secrets

Yup, I know that he was. Mrs. Lynchpin_yyz requested both our upgrades while we were on the limo-bus from NRT into Tokyo (and of course she requested mine first :D).

got an update, a friend of mine who's P requested an upgrade for his flight when checking-in

i looked at flightstats (R1J4) as well as ac.com and see the following for a dummy booking of his flight:
AC7996: Dallas to Toronto
Seats available for upgrade*


he's still waitlisted right now and when he checks the eupgrade page, gets the following message:
Because you or another passenger on your booking have already checked in for your flight(s), you may only make an upgrade request at the airport or via Web-check-in.

this might explain why lynchpin_yyz colleague got the upgrade before him

canceling check-in did NOT move him back to the normal list, he still can't request the upgrade (i guess checking in moves you to the airport list, while canceling check-in does not move you back)

i smell defect or bad business rules, that or revenue management shouldn't release R space when web check-in begins

in my yield management research, this is often a combination of art and science.... art in a sense, getting a feel on how potentially the flight might be doing from past experience..... science reviewing previous data to determine the potential outcomes.

i think this makes sense....basically there are two databases..... a reservations and an airport operational....

in the past (paper certs era), we would need to re-request upgrade because the list is not transferred over. However, i am guessing when you check in during waitlist it will transfer your specific data (name, booking reference, upgrade date/time, status, booking class) over from the reservations to the operational list.

advanced waitlisted upgrade is drawn from the reservations inventory while the airport upgrades is drawn from the operational system.

this would explain why OP had to wait until the end and his/her buddy was upgraded.

this makes sense... but if they release space when check-in starts, doesn't this mean those that check-in at the 24 hour mark are somehow disadvantaged? check-in time is the last tie-breaker for the airport list but ones strategy would be different if R space gets released in the last 24 hours, granted chances are they only release it when they're pretty sure everyone's upgrade will clear

Well we need better computer programmers to start and potential scenarious carefully thought out, designed and tweaked.

I don't think this is one if ac's priorities. I was told by the yyz concierge desk that the WL is tie broken as follows

SE
E
NOMINEE OF SE
NOMINEE OF E

But others say it ain't so. I really have no idea except that as a SE I have literally NEVER missed an upgrade when requesting it at t-7 days exactly. However I see upgrade chances around 50-70 percent of the time for my Elite family members.

but right now what we are saying is..... once you are checked in you are on the operational upgrade list, but at times HQ may review the loads last minute and those whom are not checked in early and continued to be waitlisted on the reservations database are upgraded.

(ie. a unchecked in person being upgraded to J ahead of a person that has checked in early).

if everyone appeared on the airport upgrade list, then you are correct.