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If your house originally had a cedar shake roof and it has other roof material on top, it will have to be removed and you will need all new decking. You may not be aware of this because it is not visible from the outside of the house. However, if you can see the rafters in your attic, you can see the cedar shakes. Cedar was installed to 1×3 lathe (not solid boards) and subsequently asphalt shingles were nailed over them. Building codes no longer allow this practice for a variety of reasons. When the asphalt shingles are removed, the cedar is generally brittle fragments and dust. There is a reason why it was roofed over in the first place (leaks, cupping, curling, rot) and that was probably decades ago. Now that the cedar has been entombed, it would never hold the nails of new shingles. Most older homes in this geographical area originally had either slate or a wood shake roof, so we are well versed with these installations.