A gap between the duct boot and the surrounding ceiling or wall material lets air move across that joint rather than staying sealed within the duct. Depending on pressure conditions, this can pull humid conditioned or attic air directly against the coldest part of the assembly — right where the metal boot meets the register — which is a common spot for condensation to concentrate.
Leakage further back in the run can also make a specific vent's supply air run colder or warmer than intended relative to design, changing the local dew point margin at that register even though the rest of the house feels normal.