Programs: Formerly over-entitled UA 1K, now under-entitled UA PP.
The only flexibility I've ever been able to negotiate is the time when the gate agent will clear an upgrade within the T-24 window. I'd say that I've succeeded in clearing an upgrade earlier in the window by asking nicely twice in 10 years. Both of those were domestic CPUs that were going to clear anyway. Overall, not much to get excited about.
If an agent upgraded someone that was not eligible for an upgrade ....wouldn't that be what many here decry as Shenanigans? .... just sayin.
(let me guess....if they were cleared after all eligible/entitled elites, most would say "no, its not")
Yes. I actually like the new system where the list is posted the day of the flight and you can estimate your chances. Sure, I don't know the exact formula, but it really beats the old days of having to ask if you're on the list, and what place you are in.
My first CO upgrade was as a Silver on a transcon; I asked innocently if Golds ever upgraded on that route, and they decided to "show me", not realizing that I'd asked before reaching Gold.
Recently I gave my brother my lay-flat bed from EWR to Barcelona; he wasn't feeling well and needed the sleep. He saw empties and is very smooth about asking this sort of thing; he started working them to upgrade "me". As smoothly they told him that if he was a good brother he'd give me his seat.
i occasionally have luck at out-stations when affected by severe irrops. i always ask in an irrops situation if they would be willing to reaccomodate me in first, and tell them that i am flexible for carrier, time, and connection points -- the worst they can say is no.
Programs: AA Platinum; DL Platinum; UA Gold; HH Gold; Marriott Silver; SPG Gold
I think I saw it happen once on AA out of LHR. A middle aged couple inquired about an upgrade to biz class for the flight to JFK. The agent quoted the price in dollars and they were shocked. Me, too. The wife complained that her husband was desperately ill and could not endure the trip in coach. He needed to get home to the care of his own doctor. I assumed they would be stuck in coach. Close to boarding time they were summoned to the podium and presented with new boarding passes that pleased them very much. The wife thanked the agents for their show of kindness and mercy to make this wonderful thing happen.
I was traveling on a biz class award ticket. They were seated one row in front of me and on the opposite side of the aisle. They demanded two preflight adult beverages. During the trip the ill gentleman alternated between whiskey and milk. No wonder he was not feeling well.
I've only done it once, a long time ago. I was paged to the ticketing counter to receive a seat in F on the first leg of a two-segment trip, because according to the agent, "I needed your seat in Coach to sell a last-minute fare". When I was at the connection point I laid my ticket and F boarding pass for the incoming flight down on the counter and simply asked if there was a "better seat available" than the one I'd been assigned for the next flight. The agent picked up on the cue and put me in the last seat in F, about 30 mins. before departure.
But just blatantly going up to an agent and asking to be put into First for no other reason than I just want a free upgrade someone else may be entitled to or is flying empty? No, I wouldn't ever do it. I would ask if paid counter upgrades are available, though, if sitting in F was marginally important on that flight and other options were rather expensive.
I've also been put into F as a thanks when volunteering for a bump, even if they ended up not needing my seat.
I once got my wife upgraded to PS business while she was on an award ticket. The were upgrading anyway due to Y oversell but were going to upgrade me and not her (no status on award). I asked nicely, told them it was our anniversary (it was) and offered to pay w/ miles if they bent the no upgrades on award rule. The gave it to her for free. Nice. Perhaps unfair to someone else, though.