Shutter locks from what I recall are a plastic tooth type tieback that you probably will not get out in good enough shape to reuse (especially since they get brittle with age), so unless you want to source new shutter locks, or replace with a painted head screw I would attempt to paint in place.

What are they coming out of? Pics?

Vinyl siding. I did paint the first story in place but I was hoping to take off the 2nd story shutters to avoid painting on a high ladder

I would cut the spikes loose and just replace them and paint them on a set of saw horses.

Just be sure to indicated placement (window, side, and direction) on the back of the shutter. That will save you a bunch of time.

+1. Snip the plastic plugs. Order some painted shutter screws for reattachment. You can find them right on amazon in many colors.

Thanks! Are the screws easier for reattachment than new fasteners? And would I have to drill new holes?

Replace with either correct size shutters properly installed with hinges or go without shutters. Those are known as "stick-ons".