From the T&C: "Certificate may be used only to upgrade tickets for travel by the Medallion member or one companion in the same reservation and confirmed in the same cabin as that member."

We have separate reservations. The agent said that she was cross-referencing the 2 reservations and spent a good bit of time writing comments in her record. Who the comments are for, I don't know. She also spent a few minutes figuring out the applicable rules, but in the end she put in the upgrade.

Perhaps I should just let it alone since I have what I want (at least for now), but I have until midnight to make changes to the 2 reservations before the change fee kicks in and complicates any needed changes.