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Hi Brandon!
Thanks for your input! I hope I understand your idea correct but correct me if I am wrong. I will try to explain the current logic. If the two boards that you move cards between have the same label setup then the labels will follow to the next board. However if orange is named to "Bugs" on one board and orange is named to "Issues" to the board that you are moving it to then the label will not be transferred due to different naming. So this becomes a conflict and therefore label is not retained. So if labels are named the same or not named at all the labels the card label will follow to the other board.

Best regards

DIMELO - innovation management specialist