Choose the correct type of paint for the cedar.
Painting cedar roof shingles.
Any rough treatment in your preparation will damage the visual aspect of the material as it is cedar which is a softwood.
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Your problem looks more like an issue of poor preparation between previous paint jobs.
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Nail down loose cedar shakes.
It is not all about protection.
The type of finish selected is driven by style preference.
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Like most wooden shingles however especially when painted they require care and maintenance over the course of time.
Painting weathered cedar shingles goes hand in hand with new ones.
Stains will only hold up on cedar shingles for two to three years while a quality paint will serve as an attractive finish for 10 to 15 years.
They consist of a layer of cedar mounted to either plywood or fiberboard and are attached in panel form.
Paint cedar for a more formal look.
New cedar shingles are more frequently stained than painted but painted wood shingles are much less maintenance intensive.
Exterior grade acrylic latex paint is the most dependable finish in terms of protecting cedar.
I preferred stain over full bodied paint on rough cedar sided homes because it put less build on the home.
The cedar shake shingle bureau a nonprofit trade organization warns that an experienced washer should assess a cedar siding job individually since high pressure water jets can damage wood.
Only exception to this is weathered shingles require power washing removing old decayed wood layer off.
Further the less build up of paint stain film the more the house can breathe and the less the chance of moisture related peeling.
First painting freshly milled cedar requires a paint stain unless a 100 acrylic exterior primer is used first thereby allowing a 100 solid acrylic paint to be used as final finish coats.
As with all painting surface prep is the key to success.
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It does not conceal the texture of the rough sawn lumber.