do people run into issues when splitting complimentary upgrades? last week BOS-DFW-MOS, both got upgraded no problem on first leg, on the second leg, my son was at the bottom of the list (#20) despite me clearing. the gate agent said she couldnt do it so he lost out on the last remaining seat

doing MTJ-DFW-BOS today - first leg is full, second leg has a few seats. I checked me and my son in and hes not even on the waitlist. i used twitter, they said they updated it but still not on there - am told to talk to agent at airport

reconsidering whether its worth splitting them in the future and whether people run into this often and have a good solution thanks!!