Set the nail aside.
Replace gutter nails with screws.
Get a gutter screw.
Slide it into the hole on the side of the gutter and into the ferrule.
Inspect your gutters 2.
Snug the screw up to the gutter being careful not to over tighten it.
If the nail is loose simply pull it out from the side of the gutter.
Do not let the ferrule slip away or fall off from the roof.
Do not secure the screw into the same hole where the nail was removed.
After removing the nails pins the new screws feel solid enough to hang off the gutter to do pull ups.
Then use a cordless drill to drive the screw into a new hole in the fascia board.
Tear out the nails 4.
Acquire the right hardware 3.
If it is still secured firmly use a claw hammer to pull it off.