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Here's another tutorial for painting outdoor water resistant cushions. This lady used a paint sprayer to get light even coats. Of course, she has a link for one on her website, but if you don't have one and want to try it, you could rent one. She also has a few tips that might be helpful. Wishing you the best!
Patio Cushion Rehab With Paint
How To Paint Outdoor Cushions
I Love Spray Paint!
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After painting, give the cushions a liberal coating with Scotchguard spray.
This additional coating will help to make the new finish water resistant.