Empress:
In January I was flying YYZ-YVR-YYZ with two others (Canadian Plus Basic). I was the only Gold in the group, and when I called 72hours ahead to upgrade, the agent did upgrade all three of us (after a bit of a creative story). When we got to the airport in Toronto, the check-in agent asked no questions, and simply printed off three J class boarding passes and applied the required stickers to each. The story in Vancouver was a bit different, however! I handed the agent the three tickets. He looked up the files in the computer. A glazed look came over him, as he asked me why all three of us had been upgraded. I informed him that I had worked the whole thing out with central reservations. He gazed at his terminal for a good five minutes (I was getting impatient, as I wanted to get my first look at the new domestic Empress Lounge). He then slapped out a binder with loose paper in it. He searched through for a while, and turned the binder to me and said "look, it says right here, Gold member my upgrade one travelling companion". I explained that black binder aside, reservations had approved my three person upgrade. He called through to the gate agent, and she said it was fine. about 25 minutes later I was given my boarding passes. This was right in the midst of the snow storms in Toronto, and my flight was oversold by 28 on an A320. I don't know what the check-in agent was going to do? Upgrade two of us, and put the third on the stand-by list? I don't think he would have dared!
Sorry for the long story, but it just frustrates me so much when these front line workers want to go back on what has already been promised to customers. Good luck!