The boot at a ceiling register is one of the more vulnerable points in a duct system for both leakage and insulation gaps, because it's an irregular fitting that's easy to under-insulate during installation and easy to leave slightly unsealed against the drywall. A gap there gives humid air a direct path to the coldest metal surface in the whole run.
Because that boot sits right at the ceiling, any condensation that forms has almost nowhere to go but onto the drywall, which is why sweating at a ceiling register tends to show up as visible staining sooner than sweating on a duct run buried deeper in the attic.