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asMonths := "January":"February":"March":"April":"May":"June":"July":"August":"September":"October":"November":"December";

@If(
@IsDocBeingSaved | @IsDocBeingMailed;
@Sort(@ThisValue; [CustomSort]; @Member($A; asMonths) > @Member($B; asMonths));
@ThisValue)

If you have a multi-value keyword field that contains months, you can use this as the translation formula to guarantee that months are sorted in correct order regardless of how the user entered them.