:confused: Do you caulk between old curled up cedar shake shingle sidings?

No caulking, that usually means you need to replace the bad pieces or all of it.

Cedar shake shingle siding say that 3 times.
You generally don't caulk anything that moves shingles expand and contract to get rid of leaks you need full repair

I agree, caulk is not recommended for a wood shingle due to the expansion and contraction of the wood.

If curling is not too bad, nail with 1 and 5/8'' ring shank siding nails 1'' in from edge on same line as existing nails.

If shingle cracks/will crack from nailing, then it should be replaced.

Good luck

Chuck