While digging turf or picking up items it appears polly roger will just keep trying but will be unable to give you items, requiring you to stop what you're doing so he can give them to you. There may be some other actions like attacking that haven't been checked as well.
Reporting this as a bug since when chopping down trees he is able to give you items off the ground so I assume he is supposed to be able to give you items during any action so long as you have free slots.
1) Equip polly roger hat
2) Dig up turf or pick up turf item while a lot of individual turf pieces are around
3) Polly roger will try to give some turf or other items to you but will be unable to do so until the actions are complete and you don't start a new one during that time
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