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A summer vacation home I use in Maine has an open 12' x 24' wood porch with multiple layers of Cabot solid color oil deck stain, and I'm planning on re-staining it. The stain is cracking and flaking near the edge of the porch, probably where it's covered in snow for much of the winter:

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However, the majority of the porch (away from the rail) looks just fine (yeah, could use cleaning):

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I've gone at the loose areas with a hand-held scraper; some of it comes up easy, some comes up hard, and some not at all:

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I'd like to know: how far should I go in getting the old stain up? Should I instead be renting a sander? The priority is for the results to be durable, although it would be nice for it to look good.

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Based on what I've seen in the pictures I'd say you have two option: 1) get a sander and sand the entire deck or 2) get two gallons of stain remover and spray in on the entire deck and scrape it all off. Deck stains are most durable when applied to wood and coating new stain over bare wood and then wood with old stain won't give you the results you want.

Also, are you sure the stuff on the deck is stain? It sure looks like paint, especially the way it's peeling. I bring this up because most stain removers do not remove paint. I'd suggest taking a few samples of the "stain" flakes and bring it into a paint store like Sherwin Williams and getting their advise.

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    I agree, that looks like paint rather than solid-color stain. If you intend to stain it you will need to get all of it off... – Jimmy Fix-it Aug 18 at 22:26

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